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研究生： 旁柯吉
Pankaj Vijayrao Khairnar
論文名稱： 第一部分. 分子內威悌反應策略進行多種雜環之多樣性導向合成及吡唑啉酮/噻唑酮衍生物之β-醯化反應 第二部份. 透過3-高醯基香豆素及不飽和吡唑啉酮經有機催化 (3+2) 環化反應進行螺環吡唑啉酮之不對稱合成
PART-I Intramolecular Wittig Strategy as a Powerful Tool for the Diversity-Oriented Synthesis of Heterocycles and Direct β-Acylation of Pyrazolone/Thiazolone Alkylidene Derivatives Catalyzed by Organophosphanes PART-II Enantioselective Synthesis of Spiro-pyrazolones via Organocatalytic (3+2) Cycloaddition Reaction between 3-Homoacylcoumarin and Unsaturated Pyrazolone Derivatives
指導教授： 林文偉
Lin, Wen-Wei
學位類別： 博士
Doctor
系所名稱： 化學系
Department of Chemistry
論文出版年： 2020
畢業學年度： 108
語文別： 英文
論文頁數： 583
中文關鍵詞： 威悌反應 、化學選擇性 、多樣性導向 、1,3-偶極體 、1,6-加成 、δ位-碳醯化 、鏡像選擇性 、β-醯化反應 、1,4-加成 、有機膦 、吡唑啉酮衍生物 、噻唑酮衍生物 、(3+2)環化加成反應 、3-高醯基香豆素 、螺環戊烷
英文關鍵詞： Wittig reaction., Chemoselective, Diversity-Oriented, Direct β-acylation, Functionalized Pyrazolones and Thiazolones, Spirocyclopentane
DOI URL： http://doi.org/10.6345/NTNU202000636
論文種類： 學術論文
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    • ACKNOWLEDGEMENT I ABSTRACT II ABBREVIATIONs LIST VI TABLE OF CONTENTS Part-I CHAPTER-1: “An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-Oximes” I-1-A. Introduction 2 I-1-B. Reviews and literatures I-1-B.1. Selected synthetic methods of pyrazole derivatives 4 I-1-B.2. Selected synthetic methods of isoxazole derivatives 5 I-1-B.3. Synthetic methods of chromane and chrominone oxime derivatives 8 I-1-B.4. Medicinal chemistry uses 10 I-1-C. Research motivation 11 I-1-D. Results and Discussion I-1-D.1. Reaction conditions optimization of pyrazole 63aa 17 I-1-D.2. Substrate scope of trisubstituted pyrazoles 63 19 I-1-D.3. Reaction optimization for isoxazole 67aa 22 I-1-D.4. Substrate scope of disubstituted isoxazoles 67 26 I-1-D.5. Reaction optimization for chrominone oxime 81aa and isoxazole 82aa 34 I-1-D.6. Synthesis of isoxazoles 82 and chromenone-oximes 81 36 I-1-D.7. Chemoselective synthesis of chromenone-oximes 81 38 I-1-D.8. Plausible mechanism 39 I-1-E. Conclusions 40 I-1-F. Experimental Section I-1-F.1. General aspects and materials 41 I-1-F.2. Experimental procedures 42 I-1-G. Analytical data for all new compounds 49 I-1-H. X-ray crystallographic data of selected compounds 90 I-1-I. 1H, 19F, 31P and 13C NMR spectra for all new compounds 108 I-1-J. Scanned copies of EI Mass Spectra for compounds 81 and 82 197 I-1-K. References 207 CHAPTER-2: “Diversity-Oriented Synthesis of Spiropentadiene Pyrazolones and 1H-Oxepino[2,3-c]pyrazoles from Doubly Conjugated Pyrazolones via Intramolecular Wittig Reaction” I-2-A. Introduction 211 I-2-B. Reviews and literatures 212 I-2-C. Research motivation 220 I-2-D. Results and Discussion 221 I-2-D.1. Reaction conditions optimization of spiropentadiene pyrazolones 50aa 227 I-2-D.2. Substrate scope of spiropentadiene pyrazolones 50 228 I-2-D.3. Reaction optimization of oxepino[2,3-c]pyrazoles 51ah 231 I-2-D.4. Substrate scope of 1H-oxepino[2,3-c]pyrazoles 51 232 I-2-D.4. Gram scale synthesis of 50ae and 51ah 234 I-2-D.5. Control experiments to prove the mechanism 235 I-2-D.6. Plausible reaction mechanism 239 I-2-D.7. Application of our protocol 240 I-2-E. Conclusions 243 I-2-F. Experimental Section I-2-F.1. General aspects and materials 245 I-2-F.2. Experimental procedures 246 I-2-G. Analytical data for all new compounds 248 I-2-H. X-ray crystallographic data of selected compounds 280 I-2-I. 1H 19F, 31P and 13C NMR spectra for all new compounds 292 I-2-J. References 352 CHAPTER 3: “Organophosphane-Catalyzed Direct β-Acylation of 4-Arylidene-Pyrazolones and 5-Arylidene-Thiazolones with Acyl Chlorides” I-3-A. Introduction 355 I-3-B. Reviews and literatures I-3-B.1. Selected synthetic methods for the C-C bond formation 358 I-3-C. Research motivation 363 I-3-D. Results and Discussion 365 I-3-D.1. Reaction optimization of β-acylated pyrazolones 17aa 365 I-3-D.2. Substrate scope of β-acylated pyrazolones 17 367 I-3-D.3. Substrate scope of β-acylated pyrazolones 17 respect to acyl chlorides 370 I-3-D.4. Reaction optimization of β-acylated thiazolone 30aa 374 I-3-D.5. Substrate scope of β-acylated thiazolone 30 376 I-3-D.6. Substrate scope of β-acylated thiazolone 30 respect to acyl chlorides 377 I-3-D.7. Plausible reaction mechanism 378 I-3-D.8. Application of our protocol 379 I-3-E. Conclusions 381 I-3-F. Experimental Section I-3-F.1. General aspects and materials 382 I-3-F.2. Experimental procedures 383 I-3-G. Analytical data for all new compounds 386 I-3-H. X-ray crystallographic data of selected compounds 415 I-3-I. 1H 19F, 31P and 13C NMR spectra for all new compounds 437 I-3-J. References 505 Part II CHAPTER 4: “Asymmetric Synthesis of Spiro-pyrazolones via Organocatalytic (3+2) Cycloaddition Reaction between 3-Homoacylcoumarin and Unsaturated Pyrazolone Derivatives” II-4-A. Introduction 508 II-4-B. Reviews and literatures II-4-B.1. Types of 1,3-dipole precursors 510 II-4-B.2. Reported methods for the generation of 1,3-dipole precursors 511 II-4-B.3. Importance of pyrazolones and coumarin derivatives and their synthetic applications 512 II-4-C. Research motivation 514 II-4-D. Results and Discussion II-4-D.1. Chiral catalyst screening 516 II-4-D.2. Solvent screening 518 II-4-D.3. Additives screening 519 II-4-D.4. Substrate scope of spiro-pyrazolones 29 with respect to coumarin 23 521 II-4-D.5. Substrate scope of spiro-pyrazolones 29 with respect to pyrazolone 28 522 II-4-D.6. Gram-scale reaction for the synthesis of spiro-pyrazolones 29 523 II-4-D.7. Absolute stereochemistry using X-ray 523 II-4-D.8. Proposed reaction mechanism and transition state 524 II-4-E. Conclusions 525 II-4-F. Experimental Section II-4-F.1. General aspects and materials 526 II-4-F.2. Experimental procedures 527 II-4-G. Analytical data for all new compounds 529 II-4-H. X-ray crystallographic data of selected compounds 542 II-4-I. HPLC data of all compounds 546 II-4-J. 1H 19F, 31P and 13C NMR spectra for all new compounds 564 II-4-K. References 582

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