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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
相關次數：	點閱：54 下載：0
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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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