DEVELOPMENT OF NEW MULTICOMPONENT REACTION FOR THE SYNTHISIS OF FUSED AND BRIDGED FUSED HETEROCYCLES
- Alternative Title
- 퓨즈드와 브리지퓨즈드 헤테로고리 화합물의 합성을 위한 새로운 다성분반응에 관한 연구
- Abstract
- “퓨즈드와 브리지퓨즈드 헤테로고리 화합물의 합성을 위한 새로운 다성분반응에 관한 연구”란 제목의 박사학위 논문은 총 9 장으로 구성되어 있다. 본 논문에서는 균일성촉매와 불균일성촉매를 사용하여 기능성을 갖는 퓨즈드와 브리지퓨즈드 다환헤로고리 구조의 갖는 화합물의 합성을 위한 다성분 전략을 다루고 있다. 이 연구에서 우리는 기존의 acid/base 시스템과 연관된 환경적인 위험요소를 감소시키기 위하여 최적의 재사용 촉매체계를 찾는 노력에 집중하였다. 또한 다양한 불균일성촉매들을 제조하여, 여러 가지 유용한 헤테로고리 구조를 갖는 화합물의 합성 반응에 스크린하여, 이용하였다. 일련의 다양한 퓨즈드와 브리지퓨즈드 다환헤테로고리 구조를 갖는 전구체들을 Fridel-Crafts 반응, Knoevenagel 반응, Michael 반응 그리고 6-endo-dig 반응을 통하여 우수한 수율로 쉽게 합성 할 수 있었다.
- Issued Date
- 2016
- Awarded Date
- 2016. 8
- Type
- Dissertation
- Publisher
- 부경대학교 대학원
- Affiliation
- 부경대학교 대학원
- Department
- 대학원 융합디스플레이공학과
- Advisor
- 정연태
- Table Of Contents
- I Development of New Fused and Bridged fused Heterocyclic Multicomponent Reactions 1
I.I Introduction 1
I.II Aim of this thesis 2
I.III References 4
Chapter 1. A green and convenient protocol for the synthesis of diarylmethanes via a one-pot, three-component reaction catalyzed by new silica tungstic acid (STA) under solvent free condition 5
1.1 Introduction 5
1.2 Result and Discussion 6
1.3 Conclusion 12
1.4 Experimental 12
1.4.1 Materials and methods 12
1.4.2 General procedure for the synthesis of N, N-dialkyl amino arylated β-naphthol 12
1.4.3 General procedure for the synthesis of N, N-dialkyl amino arylated Indole 12
1.4.4 Spectral Characterization dat 12
1.5 References 24
Chapter 2. Silica supported tungstic acid (STA): an efficient catalyst for the synthesis of bis-spiro piperidine derivatives under milder condition 25
2.1 Introduction 25
2.2 Result and Discussion 26
2.3 Conclusion 33
2.4 Experimental 34
2.4.1 Materials and methods 34
2.4.2 General Procedure for the synthesis SSC 34
2.4.3 General procedure for indeno[1,2-b]quinolin 34
2.4.4 General procedure for spiro[chromene-4,3’-indoline]-3-carbonitriles 35
2.4.5 Spectral Characterization data 35
2.5 References 58
Chapter 3. A metal-free tandem C−/C− bond formation approach to densely functionalized indolyl 4H-chromenes catalyzed by polystyrene supported p-toluenesulfonic acid under solvent-free conditions 60
3.1 Introduction 60
3.2 Result and Discussion 62
3.3 Conclusion 72
3.4 Experimental 72
3.4.1 Materials and methods 72
3.4.2 General procedure for the synthesis of Indolyl 4H-Chromene 72
3.4.3 Spectral Characterization data 72
3.5 References 89
Chapter 4. p-Toluenesulfonic acid doped polystyrene (PS-PTSA): solvent-free microwave assisted cross-coupling-cyclization-oxidation to build one-pot diversely functionalized pyrrole from aldehyde, amine, active methylene and nitroalkane 91
4.1 Introduction 91
4.2 Result and Discussion 92
4.3 Conclusion 96
4.4 Experimenta l96
4.4.1 Materials and methods 96
4.4.2 General procedure for the synthesis of tetrasubstituted pyrrole 96
4.4.3 Spectral Characterization data 97
4.5 References 103
Chapter 5. Molybdate sulfuric acid (MSA): an efficient solid acid catalyst for the synthesis of diversely functionalized fused imidazo[1,2-a]pyrimidines under solvent-free condition 107
5.1 Introduction 107
5.2 Result and Discussion 109
5.3 Conclusion 118
5.4 Experimental 118
5.4.1 Materials and methods 118
5.4.2 Preparation of MSA 118
5.4.3 General Procedure for the Synthesis of imidazo[1,2-a]-pyrimidine 119
5.4.4 Spectral Characterization data 119
5.5 References 137
Chapter 6. Group-assisted purification (GAP) chemistry for densely functionalized tetrahydroindazolo [3,2-b]quinazoline derivatives: facile and efficient one-pot synthesis under catalyst-free conditions 140
6.1 Introduction 140
6.2 Result and Discussion 142
6.3 Conclusion 152
6.4 Experimental 153
6.4.1 Materials and methods 153
6.4.2 General Procedure for the Synthesis of indazolo[3,2-b]quinazolin-8(5H)-one at Conventional heating 153
6.4.3 General Procedure for the Synthesis of indazolo[3,2-b]quinazolin-8(5H)-one at Ultrasound 153
6.4.4 Spectral Characterization data 154
6.5 References 176
Chapter 7. Copper-mediated synthesis of Novel fused pyrimido[1,2-b]indazole intramolecular 6-endo-dig cyclization 179
7.1 Introduction 179
7.2 Result and Discussion 181
7.3 Conclusion 186
7.4 Experimental 187
7.4.1 Materials and methods 187
7.4.2 General procedure for the synthesis of copper-catalyzed pyrimido[1,2-b]indazole 187
7.4.3 Spectral Characterization data 187
7.5 References 204
Chapter 8. Organic-base-catalyzed diversity-oriented synthesis of Novel pyrimido[1,2-b]indazole-3-carbonitrile 206
8.1 Introduction 206
8.2 Result and Discussion 208
8.3 Conclusion 213
8.4 Experimental 214
8.4.1 Materials and methods 214
8.4.2 General procedure for the synthesis of DBA-catalyzed pyrimido[1,2-b]indazole-3-carbonitrile 214
8.4.3 Spectral Characterization data 214
8.5 References 226
Chapter 9. Ultrasound assisted synthesis of diversely functionalized tetrahydro-1H-indole-4(5H)-one using Brønsted base silica sodium carbonate (SSC) as a catalyst under solvent-free condition 228
9.1 Introduction 228
9.2 Result and Discussion230
9.3 Conclusion 236
9.4 Experimental 236
9.4.1 Materials and methods 236
9.4.2 Preparation of SSC 237
9.4.3 General Procedure for the Synthesis of tetrahydro-1H-indol-4(5H)-one 237
9.4.4 Spectral Characterization data 238
9.5 References 252
Chapter 10. 254
10.1 Summary 254
10.2 List of publications 256
- Degree
- Doctor
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