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研究生： 溫斯林
R.R.Rajawinslin
論文名稱： 應用多種策略和成具有生物活性的含氮及氧雜環化合物
MULTIFACETED APPROACH TOWARDS THE SYNTHESIS OF BIOLOGICALLY ACTIVE O, N - HETEROCYCLES
指導教授： 姚清發
Yao, Ching-Fa
學位類別： 博士
Doctor
系所名稱： 化學系
Department of Chemistry
論文出版年： 2015
畢業學年度： 104
語文別： 英文
論文頁數： 301
中文關鍵詞： 四氟硼酸 、氟化反應 、環裂解 、碳-碳鍵斷裂
英文關鍵詞： Selectfluor, Ring cleavage, C-C bond cleavage, Synthetic methods, Defluorination, N-O Coupling, Heterocycles
論文種類： 學術論文
相關次數： 點閱：83  下載：13 
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    • 本文的內容分為兩部分。第一部分被細分成三個部分。 A節描述了將SelectFluor介導的氟化反應的概述。 B節描述了“將SelectFluor介導的氟化和C-C鍵斷裂環己烯稠合的異噁唑啉N-氧化物”。在本節中，一個快速的方法使用的CC鍵斷裂以及這些化合物的合成的效用長鏈氟化合物的合成進行說明。 C部分描述了“將SelectFluor介導的一鍋煮合成環己酮環的稠合異噁唑衍生物”。第二部分還細分成三個部分。 A節描述的鐵/乙酸介導的反應，還原環化反應的重要性在概述中有機合成及最近報導的從我們集團鐵/乙酸介導的協議。 B節描述了“鐵/乙酸介導的分子間串聯CC和CN鍵的形成：一個容易獲得吖啶和喹啉衍生物”。在本節中，一個快速的方法的生物活性化合物的合成通過使用鐵/乙酸進行說明。 C部分描述了“鐵/乙酸介導的合成6,7-二氫[B，D]通過分子內還原cylization [1,7]菲羅啉衍生物”。在本節中，一個簡單的方法用於多環化合物的合成通過使用鐵/乙酸以及它們的新合成的化合物的合成的效用進行了描述。

    The content of this dissertation is divided into two parts. Part I is subdivided into three sections. Section A describes the overview on Selectfluor mediated fluorination reactions. Section B describes the “Selectfluor-mediated fluorination and C–C bond cleavage of cyclohexene-fused isoxazoline N-oxides”. In this section, a rapid method for the synthesis of long chain fluoro compounds using C-C bond cleavage and the synthetic utility of these compounds are described. Section C describes the “Selectfluor mediated one-pot synthesis of cyclohexanone ring fused isoxazole derivatives”. Part II also subdivided into three sections. Section A describes the overview of iron/acetic acid mediated reactions, importance of reductive cyclization reactions in organic synthesis and the recently reported iron/acetic acid mediated protocols from our group. Section B describes the “Iron/Acetic acid mediated intermolecular tandem C-C and C-N bond formation: An easy access to acridinone and quinoline derivatives”. In this section, a rapid method for the synthesis of biologically active compounds by using iron/acetic acid is described. Section C describes the “Iron/acetic acid mediated synthesis of 6,7-dihydrodibenzo [b,j] [1,7] phenanthroline derivatives via intramolecular reductive cylization”. In this section, an easy method for the synthesis of polycyclic compounds by using iron/acetic acid and the synthetic utility of these newly synthesized compounds are described.

    Part – I, Section-A: Overview on Selectfluor mediated fluorination reactions I.A.1. Introduction 1-2 I.A.2. Common electrophilic fluorinating agents 2-3 I.A.3. Electrophilic fluorination reactions 3-4 I.A.4. Recent advances in Selectfluor mediated fluorination reactions 4-5 I.A.5. Selectfluor mediated decarboxylative fluorination reactions 5-6 I.A.6. Selectfluor as oxidizing agent 5-7 I.A.7. Selectfluor- a reagent for cyclization 7-8 I.A.8. An introduction to cyclohexene-fused isoxazoline N-oxides 8-10 I.A.9. References 12-14 Section-B: Selectfluor-mediated fluorination and C–C bond cleavage of cyclohexene-fused isoxazoline N-oxides I.B.1. Introduction 15-16 I.B.2. Result and discussions 16-24 I.B.3. Conclusion 24 I.B.4. Experimental section 24-31 I.B.5. References 32-34 Section-C: Selectfluor mediated one pot synthesis of cyclohexanone ring fused isoxazole derivatives I.C.1. Introduction 35-36 I.C.2. Result and discussions 36-43 I.C.3. Conclusion 43 I.C.4. Experimental section 43-49 I.C.5. References 49-51 Part – II Part – II, Section-A: Overview on iron/acetic acid mediated reactions II.A.1. Introduction 53 II.A.2. Recent advances in iron/acetic acid mediated reactions 54-55 II.A.3. Iron/acetic acid mediated protocols from our group 55-57 II.A.4. References 58-61 Section-B: Iron/Acetic acid mediated intermolecular tandem C-C and C-N bond formation: An easy access to acridinone and quinoline derivatives II.B.1. Introduction 63-64 II.B.2. Review of literature 64-65 II.B.3. Result and discussions 65-75 II.B.4. Conclusion 75 II.B.5. Experimental section 75-86 II.B.6. References 87-89 Section-C: Iron/acetic acid mediated synthesis of 6,7-dihydrodibenzo [b,j] [1,7] phenanthroline derivativesvia intramolecular reductive cylization II.C.1. Introduction 91-92 II.C.2. Review of literature 92-93 II.C.3. Result and discussions 94-105 II.C.4. Conclusion 105 II.C.5. Experimental section 106-123 II.C.6. References 124-129 X-ray crystallographic data 131-148 1H and 13C NMR spectral copies 149-273 List of publications 275-276

    Part – I, Section-A: Overview on Selectfluor mediated fluorination reactions

    1. (a) Ilardi, E. A.; Vitaku, E.; Njardarson , J. T. J.Med.Chem. 2014, 57, 2832. (b) Njar, V.C. O.; Brodie, A. M. H. J.Med.Chem. 2015, 58, 2077
    2. (a) Smith, B. R.; Eastman, C. M.; Njardarson, J. T. J. Med. Chem. 2014, 57 9764. (b) Gharbia, M. A.; Childers, W. E. J. Med. Chem. 2014, 57, 5525.
    3. (a) Gharbia, M. A. ; Childers, W. E. J. Med. Chem. 2013, 56, 5659. (b) Zhou, H.; Chen, J.; Meagher, J. L.; Yang, C.-Y.; Aguilar, A.; Liu, L.; Bai, L.; Cong, X.; Cai, Q.; Fang, X.; Stuckey, J. A.; Wang S. J. Med. Chem., 2012, 55, 5987. (c) Cong, X.; Cai, Q.; Fang, X.; Stuckey, J. A.; Wang, S. X.; Cai, Q.; Fang, X.; Stuckey, J. A.; Wang S. J. Med. Chem. 2012, 55, 4664. (d) Noel, A.; Powell J. Med. Chem. 2007, 50, 1720.
    4. (a) Branch , S. K.; Agranat, I. J. Med. Chem. 2014, 57, 8729. (b) Gharbia, M.A.; Childers, W. E. J. Med. Chem. 2014, 57, 5525. (c) Bruns, R. F.; Watson, I. A. J. Med. Chem. 2012, 55, 9763.
    5. (a) Ilardi, E. A.; Vitaku, E.; Njardarson, J. T.; J.Med.Chem. 2014, 57, 2832. (b) Gharbia, M.A.; Childers, W. E. J. Med. Chem. 2014, 57, 5525.
    6. (a) Nyffeler, P. T.; Duron, S. G.; Burkart, M. D.; Vincent, S. P.; Wong, C. H. Angew.Chem. Int. Ed. 2005, 44, 192. (b) Khazaei, A.; Rahmati, S.; Nezhad, A. K; Saednia, S. J. Fluorine Chem. 2012, 137, 123. (c) Krow, G. R.; Gandla, D.; Guo,W.; Centafont, R. A.; Lin, G.; Brosse, C. D.; Sonnet, P. E; Ross, C. W.; Ramjit, H. G.; Cannon, K. C. J. Org. Chem. 2008, 73, 2122.
    7. Bi, J.; Zhang, Z.; Liu, Q.; Zhang, G. Green Chem.2012, 14, 1159.
    8. Yang, L.; Ma, Y.; Song, F.; You , J. Chem.commun, 2014, 50, 3024.
    9. Wang, M.; Liu, X.; Zhou, L.; Zhu. J. Sun, X. Org.Biomol.Chem. 2015, 13,3190
    10. Ma, J.-J.; Yi, W.-B.; Lu, G.-P.; Cai, C. Org.Biomol.Chem. 2015, 13, 2890.
    11. Yi, W.-B.; Zhang, Z.; Huang, X.; Tanner, A.; Cai, C.; Zhang, W. RSC.Adv. 2013, 3, 18267.
    12. Yang, Q.; Mao, L.-L.; Yang, B.; Yang, S.-D. Org. Lett. 2014, 16, 3460.
    13. Bloom, S.; Pitts, C. R.; Woltornist, R.; Griswold, A.; Holl, M. G.; Lectka, T. Org. Lett. 2013, 15, 1722.
    14. Yin, F.; Wang, Z.; Li, Z.; Li, C. J. Am. Chem. Soc. 2012, 134, 10401.
    15. Wang, H.; Guo, L.-N.; Duan, X.-H. Chem.Commun. 2014, 50, 7382.
    16. Mizuta, S.; Stenhagen, I. S. R.; Duill, M.O.; Wolstenhulme, J.; Kirjavainen, A. K.; Forsback, S.J.; Tredwell, M.; Sandford, G.; Moore, P. R.; Huiban, M.; Luthra, S. K.; Passchier, J.; Solin, O.; Gouverneur, V. Org. Lett. 2013, 15, 2648.
    17. Patel, N. R.; Flowers, R.A. J. Org. Chem 2015, 80, 5834.
    18. Zheng, Y.; Li, Y.; Xiong, T.; Zhang, J.; Zhang, Q. Chem.Commun. 2013, 49, 8866.
    19. Zhou, J.; Jin, C.; Li, X.; Su, W. RSC.Adv, 2015, 5, 7232.
    20. Li, Y.; Li, Z.; Xiong, T.; Zhang, Q.; Zhang, X. Org. Lett. 2012, 14, 3522.
    21. Arcadi, A.; Pietropaolo, E.; Alvino, A.; Michelet, V. Org. Lett. 2013, 15, 2766.
    22. Jeong, Y.; Kim, B.-I.; Lee, J. K.; Ryu, J.-S. J. Org. Chem. 2014, 79, 6444.
    23. Zhang, J.; Wu, D.; Chen, X.; Liu, Y.; Xu, Z. J. Org. Chem. 2014, 79, 4799.
    24. Liu, R.; Lu, Z.-H.; Hu, X.-H.; Li, J.-L.; Yang, X. J.Org. Lett. 2015, 17, 1489.
    25. Zhang, J.; Wang, H.; Ren, S.; Zhang, W.; Liu, Y. Org. Lett. 2015, 17, 2920.
    26. Raihan, M. J.; Kavala, V.; Habib, P.M.; Guan, Q-Z.; Kuo, C.-W.; Yao, C.-F J. Org. Chem. 2011, 76 , 424.
    27. Raihan, M. J.; Kavala, V.; Guan, Q. Z.; Kuo, C.-W.; Kataria, S.; Shishodia, S.; Janreddy, D.; Habib, P. M.; Yao, C.-F. Adv.Synth.Catal. 2012, 354, 2251.
    28. Raihan, M. J.; Rajawinslin, R. R.; Kavala,V.; Kuo, C.-W.; Kuo, T.-S.; He, C.-H.; Huang, H. N.; Yao, C.-F. J. Org. Chem. 2013, 78, 8872.
     
    Section-B: Selectfluor-mediated fluorination and C–C bond cleavage of cyclohexene-fused isoxazoline N-oxides

    1. (a) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359. (b) Kirk, K. L. Organic Process Research & Development. 2008, 12, 305. (c) Hagan, D. O. J. Fluorine Chem. 2010, 131, 1071. (d) Kirk, K. L. J. Fluorine Chem. 2006, 127, 1013. (e) Filler, R.; Sha, R. Future Med. Chem. 2009, 1, 777. (f) Isanbor, C.; Hagan, D.; J. Fluorine Chem. 2006, 127, 303. (g) Muller, K.; Faeh, C.; Diederich, F. Science, 2007, 317, 1881.
    2. (a) Becerril, M. R.; Sazepin, C. C.; Leun, J. C. T; Okbinoglu, T.; Kennepohl, P.; Paquin, J. F.; Sammis, G. M. J. Am. Chem. Soc. 2012, 134, 4026. (b) Kuehnel, M. F.; Lentz, D.; Braun, T. Angew.Chem.Int. Ed. 2013, 52, 3328. (c) Troegel, B.; Lindel, T. Org. Lett. 2012, 14, 468. (d) Barker, T. J.; Boger, D. L J. Am. Chem. Soc 2012, 134, 13588. (e) Tian, T.; Zhong, W.H.; Meng, S.; Meng, B.; Li, J.Z J. Org. Chem. 2013, 78, 728. (f) Fukuzumi, T.; Shibata, N.; Sugiura, M.; Nakamura, S.; Toru, T. J. Fluorine Chem. 2006, 127, 548.
    3.(a) Chambers, R. D.; Okazoe, T.; Sandford, G.; Thomas, E.; Trmcic, J. J. Fluorine Chem. 2010, 131, 933. (b) Struble, M. D.; Scerba, M. T.; Siegler, M.; Lectka, T. Science, 2013, 340, 57. (c) Hennecke, U. Science, 2013, 340, 41. (d) Zhang, X.; Liao, Y.; Qian, R.; Wang, H.; Guo, Y. Org. Lett. 2005, 7, 3877. (e) Zhou, C.; Zhichao, M.; Zhenhua, G.; Chunling, F.; Shengming, M. J. Org. Chem. 2008, 73, 772. (f) Phipps, R. J.; Toste, F. D. J. Am. Chem. Soc. 2013, 135, 1268. (g) Li, Z.; Song, L.; Li, C. J. Am. Chem.Soc. 2013, 135, 4640.
    4. (a) Jones, D. M.; Lisboa, M. P.; Kamijo, S.; Dudley, G. B. J. Org. Chem. 2010, 75, 3260. (b) Kamijo, S.; Dudley, G. B. J. Am. Chem. Soc. 2005, 127, 5028. (c) Kamijo, S.; Dudley, G. B. J. Am. Chem. Soc. 2006, 128, 6499.
    5. Selected references for cyclohexene ring cleavage (a) Nicolau, K. C.; Ding, H.; Richard, J.-A.; Chen, D. Y.-K. J. Am. Chem. Soc. 2010, 132, 3815. (b) Miyamoto, K.; Sei, Y.; Yamaguchi, K.; Ochiai, M. J. Am. Chem. Soc. 2009, 131, 1382. (c) Menger, F. M.; Lu, H.; Chem. Commun. 2006, 3235. d) Ho, C.-M.; Yu, W.-Y.; Che, C.- M. Angew. Chem. Int. Ed. 2004, 43, 3303. (e) Kuhn, F. E.; Fischer, R. W.; Herrmann, W. A.; Weskamp,T. in Transition Metals for OrganicSynthesis, Vol. 2 (Eds: M. Beller, C. Bolm), WILEY-VCH: Weinheim, Germany, 2004, pp. 427-428; (f) Travis, B. R.; Narayan, R. S.; Borhan, B. J. Am. Chem. Soc. 2002, 124, 3824. (g) Sato, K.; Aoki, M.; Noyori, R. Science 1998, 281, 1646.
    6. (a) Raihan, M. J.; Kavala, V.; Guan, Q. Z.; Kuo, C.-W.; Kataria, S.; Shishodia, S.; Janreddy, D.; Habib, P. M.; Yao, C.-F. Adv.Synth.Catal. 2012, 354, 2251. (b) Raihan, M. J.; Kavala, V.; Habib, P. M.; Guan, Q. Z.; Kuo, C.- W.; Yao, C.- F. J. Org. Chem. 2011, 76, 424.
    7. (a) Dilman, A. D.; Belyakov, P. A.; Struchkova, M. I.; Arkhipov, D. E.; Korlyukov, A. Tartakovsky, V. A. J. Org. Chem. 2010, 75, 5367. (b) Junan, M.; Cahard, D. Chem. Rev. 2008, 108, 1. (c)Yasui, H.; Yamamoto, T.; Ishimaru, T.; Fukuzumi, T.; Tokunaga, E.; Akikazu, K.; Shiro, M.; Shibata, N. J. Fluorine Chem. 2011, 132, 222. (d) Lin, R.; Ding, S.; Shi, Z.; Jiao, N. Org. Lett. 2011, 13, 4498.
    8.(a) Weijun, F.; Zou, G.; Zhu, M.; Hong, D.; Deng, D.; Xun, C.; Baoming, J. J. Fluorine Chem.2009, 130, 996. (b) Verniest, G.; Hende, E. V.; Surmont, R.; Kimpe, N. D. Org. Lett. 2006, 8, 4767. (c) Kwiatkowski, P.; Beeson, T. D.; Conrad, J. C.; MacMillan, D. W.C. J. Am. Chem. Soc. 2011, 133, 1738. (d) Lubin, H.; Dupuis, C.; Pytkowicz, J.; Brigaud, T J. Org. Chem. 2013, 78, 3487.
    9. (a) Nyffeler, P. T.; Duron, S. G.; Burkart, M. D.; Vincent, S. P.; Wong, C. H. Angew.Chem. Int. Ed. 2005, 44, 192. (b) Khazaei, A.; Rahmati, S.; Nezhad, A. K.; Saednia, S. J. Fluorine Chem. 2012, 137, 123. (c) Krow, G. R.; Gandla, D.; Guo, W.; Centafont, R. A.; Lin, G.; Brosse, C. D.; Sonnet, P. E.; Ross, C. W.; Ramjit, H. G.; Cannon, K. C.J. Org. Chem. 2008, 73, 2122. (d) Rauniyar, V.; Lackner, A. D.; Hamilton, G. L.; Toste, F. D. Science, 2011, 334, 1681.
    10.(a) Olszewska, K. R.; Palacios, F.; Kafarski, P. J. Org. Chem. 2011, 76, 1170. (b) Xiao, J. C.; Shreeve, J. M. J. Fluorine Chem.2005, 126, 475. (c) Peng, W.; Shreeve, J. M. J. Org. Chem. 2005, 70, 5760. (d) Ye, C.; Twamley, B.; Shreeve, J. M. Org. Lett. 2005, 7, 3961. (e) Han, C.; Kim, E. H.; Colby, D. A. J. Am. Chem. Soc. 2011, 133, 5802.
    11. Luo, H.-Q.; Loh, T.-P. Tetrahedron Lett. 2009, 50, 1554.
    12. CCDC number of 1a is 895146. This data can be obtained free of charge from Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/datarequest/cif.

     
    Section-C: Selectfluor mediated one pot synthesis of cyclohexanone ring fused isoxazole derivatives
    1. (a) Kumar, K. A.; Jayaroopa, P. IJPCBS. 2013, 3, 294. (b) Heasley, B.; Angew. Chem. Int. Ed. 2011, 50, 8474. (c) Speranca, A.; Godoi, B.; Zeni, G. J. Org. Chem. 2013, 78, 1630.
    2. (a) Poutiainen, P.K.; Oravilahti, T.; Perakyla, M.; Palvimo, J. J.; Ihalainen, J.A.; Laatikainen, R.; Pulkkinen, J. T. J. Med. Chem. 2012, 55, 6316. (b) Frydenvang, K.; Pickering, D. S.; Greenwood, J. R.; Larsen, N. K.; Brehm, L.; Nielsen, B.; Vogensen, S. B.; Hald, H.; Kastrup, J. S.; Larsen, P. K.; Clausen, R. P. J. Med. Chem. 2010, 53, 8354. (c) Liu, J.; Yu, L. F.; Eaton, J. B.; Caldarone, B.; Cavino, K.; Ruiz, C.; Terry, M.; Fedolak, A.; Wang, D.; Ghavami, A.; Lowe, D. A.; Brunner, D.; Lukas, R. J.; Kozikowski, A. P. J. Med. Chem.2011, 54, 7280.
    3. (a) Raihan, M. J.; Kavala, V.; Kuo, C.-W.; Raju, B. R.; Yao, C.-F. Green Chem. 2010, 12, 1090. (b) Tamura, Y.; Inoue, M.; Wada, A.; Fujita, M.; Kita, Y. Chem. Pharm. Bull. 1981, 29, 3226. (c) Hashimoto, Y.; Takada, A.; Takikawa, H.; Suzuki, K. Org. Biomol. Chem. 2012, 10, 6003. (d) Denmark, S. E.; Kallemeyn, J. M. J. Org. Chem. 2005, 70, 2839. (e) Grecian, S.; Fokin, V. V. Angew. Chem. Int. Ed.2008, 47, 8285. (f) Waldo, J. P.; Larock, R. C. J. Org. Chem. 2007, 72, 9643. (g) Crossley, J. A.; Browne, D. L. J. Org. Chem.2010, 75, 5414.
    4. (a) Hansen, T. V.; Wu, P.; Fokin, V. V. J. Org. Chem. 2005, 70, 7761. (b) Tang, S.; He, J.; Sun, Y.; He, L.; She, X. J. Org. Chem.2010, 75, 1961. (c) She, Z.; Niu, D.; Chen, L.; Gunawan, M. A.; Shanja, X.; Hersh, W. H.; Chen, Y. J. Org. Chem. 2012, 77, 3627. (d) Ueda, M.; Sugita, S.; Sato, A.; Miyoshi, T.; Miyata, O. J. Org. Chem. 2012, 77, 9344. (e) Okitsu, T.; Sato, K.; Potewar, T. M.; Wada, A. J. Org. Chem. 2011, 76, 3438. (f) Kawai, H.; Sugita,Y.; Tokunaga, E.; Shibata, N. Eur. J. Org. Chem. 2012, 1295.
    5. (a) Kuehnel, M. F.; Lentz, D; Braun, T. Angew. Chem. Int. Ed. 2013, 52, 3328. (b) Amii, H.; Uneyama, K. Chem. Rev. 2009, 109, 2119. (c) Zhang, L.; Zhang, W.; Liu, J.; Hu, J. J. Org. Chem. 2009, 74, 2850. (d) Sung, K.; Lagow. R. J. J. Chem. Soc. Perkin Trans1. 1998, 637. (e) Nakamura, Y.; Uneyama, K. J. Org. Chem. 2007, 72, 5894. (e) Volkova, Y. A.; Averina, E. B.; Grishin, Y. K.; Bruheim, P.; Kuznetsova, T. S.; Zefirov, N. S. J. Org. Chem. 2010, 75, 3047. (f) Burkhard, J. A.; Tchitchanov, B. H.; Carreira, E. M. Angew. Chem. Int. Ed. 2011, 50, 5379.
    6. Rajawinslin, R. R.; Raihan, M. J.; Janreddy, D.; Kavala, V.; Kuo, C.-W.; Kuo, T.-S.; Chen, M.-L.; He, C.-H.; Yao, C.-F.Eur. J. Org. Chem. 2013, 5743.
    7. (a) Nyffeler, P. T.; Duron, S. G.; Burkart, M. D.; Vincent, S. P.; Wong, C. H. Angew. Chem. 2005, 117, 196. (b) Rauniyar, V.; Lackner, A. D.; Hamilton, G. L.; Toste, F. D. Science 2011, 334, 1681.
    8. (a) Raihan, M. J.; Kavala, V.; Guan, Q.-Z.; Kuo, C.-W.; Kataria, S; Shishodia, S.; Janreddy, D.; Habib, P. M.; Yao, C.-F. Adv. Synth. Cat. 2012, 354, 2251. (b) Raihan, M. J.; Rajawinslin, R. R.; Kavala,V.; Kuo, C.-W.; Kuo, T.-S.; He,C.-H.; Huang, H. N.; Yao, C.-F. J. Org. Chem., 2013, 78, 8872. (c) Raihan, M. J.; Kavala, V.; Habib, P. M.; Guan, Q.-Z.; Kuo, C.-W.; Yao, C.-F. J. Org. Chem. 2011, 76, 424.
    9. Luo, H.-Q.; Loh, T.-P. Tetrahedron Lett. 2009, 50, 1554.
    10.CCDC-955136 (1a) and CCDC-989222 (16a) contain the supplementary crystallographicdata for this paper. These data can be obtained free ofcharge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk/data_request/cif.
     
    Part – II, Section-A: Overview on iron/acetic acid mediated reactions
    1. (a) Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875. (b) Singh, V.; Batra, S. Tetrahedron, 2008, 64, 4511. (c) Basavaiah, D.; Reddy, B. S.; Badsara, S. S. Chem. Rev. 2010, 110, 5447.
    2. (a) Somei, M.; Inoue, S.; Tokutake, S.; Yamada, F.; Kaneko, C. Chem.Pharm.Bull. 1981, 29, 726. (b) Lee, K. Y.; Kim, S. C.; Kim, J. N. Bull.Korean Chem.Soc. 2005, 26, 1109.
    3. (a) Zhichkin, P.; Kesicki, E.; Treiberg, J.; Bourdon, L.; Ronsheim, M.; Ooi, H. C.; White, S.; Judkins, A.; Fairfax, D. Org. Lett. 2007, 9, 1415. (b) Piper, J. R.; Stevens, F.J. J. Heterocycl. Chem., 1966, 3, 95.
    4. (a) Mamedov, V.A.; Saifina, D.F.; Gubaidullin, A.T.; Ganieva,V.R.; Kadyrova, S.F.; Rakov, D.V.; Rizvanov, D. K.; Sinyashin, O. G. Tetrahedron Lett. 2010, 51, 6503. (b) Novellino, L.; d'Ischia, M.; Prota, G. Synthesis, 1999, 793.
    5. Singh.V.; Kanojiya, S.; Batra, S.Tetrahedron , 2006, 62, 10100.
    6. (a) Sandelier, M.J.; DeShong, P.Org. Lett., 2007, 9, 3209. (b) Dagommer, I.G.; Gastaud, P.; RajanBabu, T. V. Org. Lett. 2001, 3, 2053.
    7. Muchowski, J. M.; Maddox, M. L. Can. J. Chem. 2004, 82, 461.
    8. (a) Gusy, V.; Brassard, P. J. Heterocycl. Chem. 1987, 24, 1649. (b) Owsley, D. C.; Bloomfield, J. J. Synthesis, 1977, 118. (c) Raucher, S.; Koolpe, G. A. J. Org. Chem. 1983, 48, 2066.
    9.Somei, M.; Kato, K.; Inoue, S. Chem. Pharm. Bull., 1980, 28, 2515.
    10. Buchwald, S. L.; Rutherford, J. L.; Rainka, M. P. J. Am. Chem. Soc. 2002, 124, 15168.
    11. Ma, Y.; Zhang, Y. J.Chem. Res. 2000, 388.
    12. (a) Diedrich, C. L.; Haase, D.; Saak, W.; Christoffer, J. Eur. J. Org. Chem., 2008, 1811. (b) McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257.
    13. Cruces, J.; Estévez, J.C.; Estévez, R. J.; Castedo, L. Heterocycle 2000, 53, 1041.
    14. Suzuki, H.; Gyoutoku, H.; Yokoo, H.; Shinba, M.; Sato, Y.; Yamada, H.; Murakami, Y. Synlett. 2000, 8, 1196.
    15. Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242.
    16. Macías, F.A.; Marín, D.; Bastidas, A.O.; Castellano, D.; Simonet, A.M.; Molinillo, J.M.G. J. Agric. Food Chem. 2005, 53, 538
    17. Bentley, J. M.; Davidson, J. E.; Duncton, M. A. J.; Giles, P. R.; Pratt, R. M. Synth. Commun. 2004, 34, 2295.
    18. (a) Ramesh, C.; Lei, P. M.; Janreddy, D.; Kavala, V.; Kuo, C.-W.; Yao, C.-F. J. Org. Chem. 2012, 77, 8451. (b) Janreddy, D.; Kavala, V.; Bosco, J. W.; Kuo, C.-W. Yao, C. -F. Eur. J. Org. Chem. 2011, 2360. c) Ramesh, C.; Kavala, V.; Raju, B. R.; Kuo, C.-W.; Yao, C.-F. Tetrahedron Lett. 2010, 51, 5234. (d) Ramesh, C.; Raju, B. R.; Kavala,V.; Kuo, C.-W.; Yao, C.-F. Tetrahedron, 2011, 67, 1187.(e) Ramesh, C.; Kavala, V.; Raju, B. R.; Kuo, C.-W.; Yao, C.-F. Tetrahedron Lett. 2009, 50, 4037.
    19. Basavaiah, D.; Reddy, R. M.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron, 2002, 58, 3693.
    20. Basavaiah, D.; Rao, J. S.; Reddy, R.J. J. Org. Chem. 2004, 69, 7379.
    21. Jónsson, S.; Arribas, C. S.; Wendt, O. F.; Siegel, J. S.; Wärnmark, K. Org. Biomol. Chem. 2005, 3, 996.
    22. Basavaiah, D.; Reddy, R. J.; Rao, J. S. Tetrahedron Lett. 2006, 47, 73.
    23. Basavaiah, D.; Aravindu, K. Org. Lett. 2007, 9, 2453.
    24. Basavaiah, D.; Reddy, K. R. Tetrahedron, 2010, 66, 1215.
    25. (a) Ramesh, C.; Kavala,V.; Raju, B. R.; Kuo, C.-W.; Yao, C.-F. Tetrahedron Lett. 2009, 50, 4037. (b) Ramesh, C.; Kavala, V.; Raju, B. R.; Kuo, C.-W.; Yao, C.-F. Tetrahedron Lett. 2010, 51, 5234. c) Janreddy, D.; Kavala, V.; Bosco, J.W.; Kuo, C.-W.; Yao, C.-F. Eur. J. Org. Chem. 2011, 2360. (d) Ramesh, C. Raju, B. R.; Kavala, V.; Kuo, C.-W.; Yao, C.-F. Tetrahedron, 2011, 67, 1187. (e) Ramesh, C.; Lei, P. M.; Janreddy, D.; Kavala, V.; Kuo, C.-W. Yao,C.-F. J. Org. Chem.,2012, 77, 8451.
    26. Ramesh, C.; Kavala, V.; Raju, B. R.; Kuo, C.-W.; Yao, C.-F. Tetrahedron Lett.,2009, 50, 4037.
    27. Ramesh, C.; Kavala, V.; Raju, B. R.; Kuo, C.-W.; Yao, C.-F. Tetrahedron Lett. 2010, 51, 5234.
    28. Janreddy, D.; Kavala, V.; Bosco, J. W.; Kuo, C.-W.; Yao, C.-F. Eur. J. Org. Chem. 2011, 2360.
    29. Ramesh, C.; Raju, B. R.; Kavala, V.; Kuo, C.-W.; Yao, C.-F.Tetrahedron, 2011, 67, 1187.
    30. Janreddy, D.; Kavala, V.; Bosco, J.W.; Kuo, C.-W.; Yao, C.- F. Eur. J. Org. Chem. 2011, 2360.
    31. Ramesh, C.; Lei, P. M.; Janreddy, D.; Kavala, V.; Kuo, C.-W.; Yao, C.- F. J. Org. Chem. 2012, 77, 8451.
     
    Section-B: Iron/Acetic acid mediated intermolecular tandem C-C and C-N bond formation: An easy access to acridinone and quinoline derivatives
    1. (a) Shutske, G. M.; Tomer IV, J. D. J. Heterocycl.Chem. 1993, 30, 23. (b) Paloque, L.; Verhaeghe, P.; Casanova, M.; Ducros, C. C.; Dumètre, A.; Mbatchi, L.; Hutter, S.; Rabet, M. K.; Laget, M.; Remusat, V.; Rault, S.; Rathelot, P.; Azas, N.; Vanelle, P. Euro. J. Med. Chem. 2012, 54, 75. (c) Mai, A.; Rotili, D. Tarantino, D.; Ornaghi, P.; Tosi, F.; Vicidomini, C.; Sbardella, G.; Nebbioso, A.; Miceli, M.; Altucci, L; Filetici, P. J. Med. Chem. 2006, 49, 6897. (d) Korhonen, L. E.; Turpeinen, M.; Rahnasto, M.; Wittekindt, C.; Poso, A. Pelkonen, O.; Raunio, H.; Juvonen, R.O. Br. J. Pharmacol. 2007, 150, 932.
    2. Marquise, N.; Harford, P. J.; Chevallier, F.; Roisnel, T.; Dorcet, V.; Gagez, A. L.; Sable, S.; Picot, L.; Thiery, V.; Wheatley, A. E. H.; Gros, P. C.; Mongin, F. Tetrahedron, 2013, 69, 10123.
    3. (a) Ornaghi, P.; Rotili, D.; Sbardella, G.;Mai, A.; Filetici, P. Biochem. Pharm., 2005, 70, 911. (b)Smith, A. T.; Livingston, M. R.; Mai, A.; Filetici, P.; Queener, S. F.; Sullivan, W. J. Antimicrob. Agents Chemother. 2007, 51, 1109.
    4.(a) Mulakayala, N.; Rambabu, D.; Raja, M. R.; Chaitanya, M.; Kumar, C. S.; Kalle, A. M.; Krishna, G. R.; Reddy, C. M. ; Basaveswararao, M. V.; Pal, M. Bioorg.Med.Chem. 2012, 20, 759. (b) Prasad, J. V.; Reddy, J. S.; Ravikumar, N.; Solomon, K. A.; Gopikrishna , G. J.Chem.Sci. 2011, 123, 673.
    5. Yapi, A. D.; Desbois, N.; Chezal, J. M.; Chavignon, O.; Teulade, J. C.; Valentin, A.; Blache,Y. Euro. J. Med. Chem. 2010, 45, 2854.
    6. Joshi, A. A.; Narkhede, S. S.; Viswanathan, C. L. Bioorg. Med. Chem.Lett. 2005, 15, 73.
    7. Dube, D.; Blouin, M.; Brideau, C.; Chan, C.C.; Desmarais, S.; Ethier, D.; Falgueyret, J. P.; Friesen, R. W.; Girard, M.; Girard, Y.; Guay, J.; Riendeau, D.; Tagari, P.; Young, R. N. Bioorg. Med. Chem. Lett. 1998, 8, 1255.
    8. (a) Muruganantham, N.; Sivakumar, R.; Anbalagan, N.; Gunasekaran, V.; Leonard, J. T. Bio. Pharm. Bull. 2004, 27, 1683. (b) Martirosyan, A. R.; Bata, R. R.; Freeman, A. B.; Clarke, C. D.; Howard, R.L.; Stroble, J. S. Biochem. Pharmacol. 2004, 68, 1729.
    9. Shutske, G. M.; Tomer, J. D. J. Heterocycl.Chem. 1993, 30, 23.
    10. (a) Contelles, J. M.; Mayoral, E. P.; Samadi, A.; Carreiras, M. C.; Soriano, E.Chem. Rev., 2009, 109, 2652. (b) Jia, C. S.; Zhang, Z.; Tub, S. J.; Wang, G. W. Org. Biomol. Chem. 2006, 4, 104. (c) Zheng, H.; Liu, J.; Mei, Y. J.; Shi, Q. Y.; Zhang, P. F. Catal Lett. 2012, 142, 573. (d) Xing, R. G.; Li, Y. N.; Liu,Q.; Han, Y. F.; Wei, X.; Li, J.; Zhou, B. Synthesis. 2011, 13, 2066. (e) Edmondson, S. D.; Mastracchio, A.; Parmee, E. R. Org. Lett. 2000, 2, 1109. (f) Asherson, J. L.; Bilgic, O.; Young, D. W. J. Chem. Soc., Perkin Trans. 1, 1981, 3041.
    11. (a) Camps, R. Arch. Pharm. 1899, 237, 659. (b) Skraup, H. Ber. Dtsch.Chem.Ges. 1880, 13, 2086. (c) Friedlander, P. Ber.Dtsch. Chem. Ges. 1882, 15, 2572. (d) Manske, R. H. F.; Kulka, M. Org. React. 1953, 7, 59. (e) Fehnel, E. A. J. Heterocycl.Chem. 1967, 4, 565. (f) Cheng, C.-C.; Yan, S.-J. Org. React. 1982, 28, 37.
    12. Shutske, G.M.; Tomer IV, J. D. J. Heterocycl.Chem. 1993, 30, 23.
    13. Boyd, D. R.; Davies, J. H.; Hamilton, L.; McCullough, J. J.; Malone, J. F.; Porter, H. P.; Smith, A. J. Org. Chem., 1994, 59, 984.
    14. Sridharan, V; Ribelles, P.; Ramos, M. T.; Menendez, J. C. J. Org. Chem. 2009, 74, 5715.
    15.Shen, Q.; Wang, L.; Yu, J.; Liu, M.; Qiu, J.; Fang, L.; Guo,F.;Tang, J. Synthesis 2012, 44, 389.
    16. Yu, Z. H.; Zheng, H. F.; Yuan, W.; Tang, Z. L.; Zhang, A. D.; Shi, D.Q. Tetrahedron 2013, 69, 8137.
    17. Anand, N.; Chanda, T.; Koley, S.; Chowdhury, S; Singh, M. S. RSC Adv. 2015, 5, 7654.
    18. (a) Wang, G. W.; Miao, C. B. Green Chem. 2006, 8, 1080. (b) Miri, R.; Motamedi, R.; Rezaei, M. R.; Firuzi1, O.; Javidnia, A.; Shafiee, A. Arch. Pharm. Chem. Life Sci. 2011, 2, 111. (c) Clarke, K. M.; Clair, J. J.; Burkart, M. D. J. Org. Chem. 2005, 70, 3709.
    19. (a) Fang, Y.; Larock, R. C. Tetrahedron 2012, 68, 2819. (b) Kiselev, E.; Dexheimer, T. S.; Pommier, Y.; Cushman, M. J. Med. Chem. 2010, 53, 8716.
    20. CCDC- 998617 (1a), CCDC- 998615 (31a) and CCDC- 998616 (I) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
     
    Section-C: Iron/acetic acid mediated synthesis of 6,7-dihydrodibenzo [b,j] [1,7] phenanthroline derivativesvia intramolecular reductive cylization
    1. (a) Baudoin, O.; Marchand, C.; Teulade-Fichou, M. P.; Vigneron, J. P.; Sun, J.-S.; Garestier, T.; Helene; Lehn, J.-M. Chem. Eur. J. 1998, 4, 1504. b) Bakali, J. E.; Klupscha, F.; Guédinb, A.; Brassart, B.; Fontaine, G.; Farce, A.; Roussel, P.; Houssin, R.; Bernier, J. –L; Chavatte, P.; Mergny, J.-L; Rioub, J.-F.; Hénicharta, J. -P. Bioorg. Med. Chem. Lett. 2009, 19, 3434. c) Alberti, P.; Lacroix, L.; Guittat, L.; Helene, C.; Mergny, J.-L. Mini. Rev. Med.Chem. 2003, 3, 23.
    2. Teulade-Fichou, M. P.; Carrasco, C.; Guittat, L.; Bailly, C.; Alberti, P.; Mergny, J. L.; David, A.; Lehn, J. M.; Wilson,W. D. J. Am. Chem. Soc. 2003, 125, 4732.
    3. (a) Alberti, P.; Schmitt, P.; Nguyen, C.-H.; Rivalle, C.; Hoarau, M.; Grierson, D.S.; Mergny, J.-L. Bioorg. Med. Chem. Lett. 2002, 12, 1071. b) Keppler, M.; Zegrocka, O.; Strekowski, L.; Foxa, K. R. FEBS Lett. 1999, 447, 223. c) Teulade-Fichou, M. P.; Perrin, D.; Boutorine, A.; Polverari, D.; Vigneron, J.-P.; Lehn, J. -M.; Sun, J. -S.; Garestier, T.; Helene, C. J. Am. Chem. Soc. 2001, 123, 9283.
    4. (a) Artese, A.; Costa, G.; Distinto, S.; Moraca, F.; Ortuso, F.; Parrotta, L.; Alcaro, S. Eur. J. Med. Chem. 2013, 68, 139. b) Delfourne, E.; Darro, F.; Subielos, N. B.; Decaestecker, C.; Bastide, J.; Frydman, A.; Kiss, R. J. Med. Chem. 2001, 44, 3275. c) Petersen, I. N.; Crestey, F.; Kristensen, J. L. Chem. Commun. 2012, 48, 9092.
    5. (a) Dallavalle, S.; Merlini, L.; Beretta, G. L.; Tinelli, S.; Zunino, F. Bioorg. Med. Chem. Lett. 2004, 14, 5757. b) Harayama, T.; Hori, A.; Serban, G.; Morikami, Y.; Matsumoto, T.; Abe, H.; Takeuchi, Y. Tetrahedron, 2004, 60, 10645. c) Chavan, S. P.; Sivappa, R. Tetrahedron 2004, 60, 9931. d) Mason, J. J.; Bergman, J. Org. Biomol.Chem. 2007, 5, 2486. e) Cagir, A.; Jones, S. H.; Gao, R.; Eisenhauer, B. M.; Hecht, S. M. J.Am.Chem.Soc. 2003, 125, 13628.
    6. (a) Wuand, F.; Thummel, R. P. Inorg.Chim.Acta. 2002, 327, 26. b) Jahng, Y.; Hazelrigg, J.; Kimball, D.; Riesgo, E.; Wu, F.; Thummel, R. P. Inorg.Chem. 1997, 36, 5390. c) Hu,Y-Z.; Zhang, G.; Thummel, R. P. Org. Lett. 2003, 5, 2251. d) Cucciolito, M. E.; Vitagliano, A. Organometallics, 1992, 11, 3954. e) Mergny, J.-L.; Lacroix, L.; Teulade-Fichou, M.-P.; Hounsou, C.; Guittat, L.; Hoarau, M.; Arimondo, P. B.; Vigneron, J.-P.; Lehn, J.-M.; Rioui, J.-F.; Garestier, T.; Helene, C. Proc.Natl.Acad. Sci. 2001, 98, 3062.
    7. Albano, G.; Belser, P.; Cola, L. D.; Gandolfi, M. T. Chem. Commun. 1999, 1171.
    8. (a) Sridharan, V.; Ribelles, P.; Ramos, T. J.; Menendez, C. J. Org. Chem., 2009, 74, 5715. b) Baudoin, O.; Teulade-Fichou, M.-P.; Vigneron, J.-P.; Lehn, J.-M. J. Org. Chem. 1997, 62, 5458. c) Jacquelin, C.; Saettel, N.; Hounsou, C.; Teulade-Fichou, M.-P. Tetrahedron Lett. 2005, 46, 2589. d) Jahng, Y.; Hazelrigg, J.; Kimball, D.; Riesgo, E.; Wu, F.; Thummel, R. P.; Inorg. Chem., 1997, 36, 5390. e) Thummel, R. P.; Lefoulon, F. J. Org. Chem. 1985, 50, 666.
    9. (a) Henseler, A. H.; Ayats, C.; Peric, M. A. Adv. Synth.Catal. 2014, 356, 1795. b) Maya, V.; Raj, M.; Singh, V. K. Org. Lett. 2007, 9, 2593. c) Luo, S.; Li, J.; Xu, H.; Zhang; L. Cheng, J.-P.Org. Lett. 2007, 9, 3675. d) Tang, Z.; Yang, Z.-H.; Chen, X.-H.; Cun, L.-F.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. J. Am. Chem. Soc. 2005, 127, 9285. e) Hayashi, Y.; Sumiya, T.; Takahashi, J.; Gotoh, H.; Urushima, T. Shoji, M. Angew. Chem. Int. Ed. 2006, 45, 958. f) Zhou, Y.; Shan, Z.J. Org. Chem. 2006, 71, 9510.
    10. (a) Ramesh, C.; Lei, P. M.; Janreddy, D.; Kavala, V.; Kuo, C.-W.; Yao, C.-F. J. Org. Chem. 2012, 77, 8451. (b) Janreddy, D.; Kavala, V.; Bosco, J. W.; Kuo, C.-W.; Yao, C.-F. Eur. J. Org. Chem. 2011, 2360. (c) Ramesh, C.; Kavala, V.; Raju, B. R.; Kuo, C.-W.; Yao, C.-F. Tetrahedron Lett. 2010, 51, 5234. (d) Ramesh, C.; Raju, B. R.; Kavala, V.; Kuo, C.-W.; Yao, C.-F. Tetrahedron 2011, 67, 1187. (e) Ramesh, C.; Kavala, V.; Raju, B. R.; Kuo, C.-W.; Yao, C.-F. Tetrahedron Lett. 2009, 50, 4037. (f) Bolm, C.; Legros, J.; Paih, J. L.; Zani,L. Chem. Rev. 2004, 104, 6217. (g) Diedrich, C. L.; Haase, D.; Saak, W.; Christoffers, J.Eur. J. Org. Chem. 2008, 1811. (h) McNaughton, B. R.; Miller, B. L. Org. Lett. 2003, 5, 4257. (i) Bryson, T. A. Gibson, J. M.; Stewart, J. J.; Voegtle, H.; Tiwari, A.; Dawson, J. H.; Marley, W.; Harmon, B. Green Chem. 2003, 5, 177. (j) Li, A.-H.; Beard, D. J.; Coate, H.; Honda, A.; Kadalbajoo, M.; Kleinberg, A.; Laufer, R.; Mulvihill, K. M.; Nigro, A.; Rastogi, P.; Sherman, D.; Siu, K. W.; Steinig, A. G.; Wang, T.; Werner, D.; Crew, A. P.; Mulvihill, M. J. Synthesis, 2010, 10, 1678.
    11. Rajawinslin, R. R.; Gawande, S. D.; Kavala, V.; Huang, Y.-H.; Kuo, C.-W.; Kuo, T.-S.; Chen, M.-L.; He, C.-H.; Yao, C.-F. RSC Adv. 2014, 4, 37806.
    12. (a) Shutske, G. M.; Tomer IV, J. D. J. Heterocycl. Chem. 1993, 30, 23. (b) Paloque, L.; Verhaeghe, P.; Casanova, M.; Ducros, C. C.; Dumetre, A.; Mbatchi, L.; Hutter, S.; Rabet, M. K.; Laget, M.; Remusat, V.; Rault, S.; Rathelot, P.; Azas, N.; Vanelle, P. Euro. J. Med. Chem., 2012, 54, 75. d) Ornaghi, P.; Rotili, D.; Sbardella, G.; Mai, A.; Filetici, P. Biochem Pharmacol. 2005, 70, 911. e) Mulakayala, N.; Rambabu, D.; Raja, M. R.; Chaitanya, M.; Kumar, C. S.; Kalle, A. M.; Krishna, G. R.; Reddy, C. M.; Basaveswararao, M. V.; Pal, M. Bioorg. Med. Chem. 2012, 20, 759. f) Yapi, A. D.; Desbois, N.; Chezal, J. M.; Chavignon, O.; Teulade, J. C.; Valentin, A.; Blache, Y. Eur.J. Med. Chem. 2010, 45, 2854. g) Joshi, A. A.; Narkhede, S. S.; Viswanathan, C. L. Bioorg. Med. Chem. Lett. 2005, 15, 73.
    13. (a) Gawande, S. D.; Zanwar, M. R.; Kavala, V.; Kuo, C-W.; Rajawinslin, R. R.; Yao, C.-F. Adv. Synth. Catal. 2015, 357, 168. b) Gawande, S. D.; Kavala, V.; Zanwar, M. R.; Kuo, C.-W.; Huang, W.-C.; Kuo, T.-S.; Huang, H.-N.; He, C.-H.; Yao, C.-F. Adv. Synth. Catal. 2014, 356, 2599. c) Gawande, S. D.; Kavala, V.; Zanwar, M. R.; Kuo, C.-W.; Huang, H.-N.; He, C.-H.; Kuo T.-S.; Yao, C.-F. Adv. Synth.Catal. 2013, 355, 3022. d) Zanwar, M. R.; Gawande, S. D.; Kavala, V.; Kuo, C.-W.; Yao, C.-F. Adv. Synth. Catal. 2014, 356, 3849.
    14. Borsche, V.W.; Roemmich, M. W.; Barthenheier, J. Eur. J. Org. Chem. 1942, 550, 160.
    15. Sridharan, V; Ribelles, P.; Ramos, M. T.; Menendez, J. C. J. Org. Chem. 2009, 74, 5715.
    16. Thummel, R. P.; Lefoulon, F. J. Org. Chem. 1985, 50, 666.
    17. Sridharan, V; Ribelles, P.; Ramos, M. T.; Menendez, J. C. J. Org. Chem. 2009, 74, 5715.
    18. (a) Sultan, A.; Raza, A. R.; Abbas, M.; Khan, K. M.; Tahir, M. N.; Saari, N. Molecules, 2013, 18, 10081. (b) Kumar, D.; Kaur, G.; Negi, A.; Kumar, S.; Singh, S.; Kumar, R. Bioorg. Chem. 2014, 57, 57. (c) Braulio, I.; Harlem, T.; Jairo, Q.; Rodrigo, A.; Manuel, N.; Adolfo, S.; Maximiliano, S.; Susana, Z.; John, L. Heterocycl. Commun. 2003, 9, 153. (d) Karthikeyan, G.; Perumal, P. T. J. Heterocyclic Chem. 2004, 41, 1039.
    19. (a) Karak, M.; BarbosaL. C. A.; Hargaden, G. C. RSC Adv. 2014, 4, 53442. b) Thomas, A. M.; Sujatha, A.; Anilkumar, G. RSC Adv. 2014, 4, 21688. c) Bolliger, J. L.; Frech, C. M. Adv. Synth. Catal. 2009, 351, 891. d) Vlaar, T.; Ruijter, E.; Orru, R. V. A. Adv. Synth. Catal. 2011, 353, 809. e) Liang, Y.; Xie, Y.-X.; Li, J.-H. J. Org. Chem. 2006, 71, 379.
    20. (a) Herve, G.; Sartori, G.; Enderlin, G.; Mackenzie, G.; Len, C. RSC Adv. 2014, 4, 18558. b) Billingsley, K. L.; Anderson K. W.; Buchwald, S. L. Angew. Chem. Int. Ed. 2006, 45, 3484. c) Kirchhoff, J. H.; Netherton, M. R.; Hills, I. D.; Fu, G. C. J.Am.Chem.Soc., 2002, 124, 13662. d) Rossi, R.; Bellina, F.; Lessi, M. Adv. Synth. Catal. 2012, 354, 1181. e) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
    21. (a) Chow, W. K.; Yuen, O. Y.; Choy, P. Y.; So, C. M.; Lau, C. P.; Wong, W.T.; Kwong, F. Y. RSC Adv. 2013, 3, 12518. b) Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508; c) Thompson, A. L. S.; Kabalka, G. W.; Akula, M. R.; Huffman, J. W. Synthesis, 2005, 547. d) Takagi, J.; Kamon, A.; Ishiyamaand, N. Miyaura, Synlett. 2002, 11, 1880. e) Takagi, J.; Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Am. Chem. Soc. 2002, 124, 8001.
    22. (a) Leermann, T.; Lerouxand, F. R.; Colobert, F. Org. Lett. 2011, 13, 4479. b) Murphy, J. M.; Tzschucke, C. C.; Hartwig, J. F. Org. Lett. 2007, 9, 757.
    23. Curini, M.; Epifano, F.; Genovese, S.; Marcotullio, M. C.; Rosati, O. Org. Lett. 2005, 7, 1331.
    24. (a) Nyffeler, P. T.; Duron, S. G.; Burkart, M. D.; Vincent S. P.; Wong, C. H. Angew. Chem. 2005, 117, 196. b) Khazaei, A.; Rahmati, S.; Nezhad, A. K.; Saednia, S. J. Fluorine Chem., 2012, 137, 123. c) Krow, G. R.; Gandla, D.; Guo, W.; Centafont, R. A.; Lin, G.; Brosse, C. D.; Sonnet, P. E.; Ross, C. W.; Ramjit, H. G.; Cannon, K. C. J. Org. Chem. 2008, 73, 2122.
    25. Rajawinslin, R.R.; Raihan, M. J.; Janreddy, D.; Kavala, V.; Kuo, C.-W.; Kuo, T.-S.; Chen, M.-L.; He, C.-H.; Yao, C.-F. Eur. J. Org. Chem., 2013, 5743. b) Rajawinslin, R. R.; Raihan, M. J.; Janreddy, D.; Kavala, V.; Kuo, C.-W.; Kuo, T.-S.; Chen, M.-L.; He, C.-H.; Yao, C.-F. Tetrahedron 2014, 70, 7505.
    26. (a) Raihan, M. J.; Kavala, V.; Guan, Q. Z.; Kuo, C.-W.; Kataria, S.; Shishodia, S.; Janreddy, D.; Habib, P. M.; Yao, C.-F. Adv. Synth.Catal. 2012, 354, 2251. b) Raihan, M. J.; Rajawinslin, R. R.; Kavala, V.; Kuo, C.-W.; Kuo, T.-S.; He, C.-H.; Huang, H. N.; Yao,C.-F.J. Org. Chem., 2013, 78, 8872.
    27. (a) Prakash, G. K. S.; Mathew, T.; Hoole, D.; Esteves, P. M.; Wang, Q.; Rasul, G.; Olah, G. A. J. Am. Chem. Soc. 2004, 126, 15770. b) Wu, H.; Hynes, J. J.Org. Lett. 2010, 12, 1192.
    28. CCDC numbers1050602 (4a) and 1052475 (5f), contains the supplementary crystallographic data for this paper. This data can be obtained free of charge from The Cambridge crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif

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