DEVELOPMENT OF NEW METHODOLOGIES FOR THE SYNTHESIS OF SPIRO-FUSED AND N-HETEROCYCLIC COMPOUNDS THROUGH MULTICOMPONENT REACTION
- Alternative Title
- 다성분반응을 통한 스파이로 접합 및 N-헤테로고리 화합물의 새로운 합성법 개발 연구
- Abstract
- The thesis entitled “Development of New Methodologies for The Synthesis of Spiro-fused and N-Heterocyclic Compounds Through Multicomponent Reaction” is divided into eight chapters. In this context, the present thesis deals with the application of multicomponent strategies for the synthesis of spiro-fused, polyheterocycles and N-heterocyclic frameworks, by using homogeneous and heterogeneous catalysts. In this concern, we mainly focused to find a best reusable catalytic system an attempt to reduce the environmental hazards associated with the conventional acid/base system. So various, heterogeneous catalysts have been prepared, screened and utilized for the synthesis of various useful heterocyclic frameworks. A series of diverse spiro-fused, polyheterocycles and N-heterocyclic precursor were easily prepared in excellent yields via the Knoevenagel reaction, Mannich reaction, Michael reaction and cyclization reaction. These methodological transformationsare tolerant of a variety of functionalities, thus giving broad substrate scope.
논문 제목은 “다성분반응을 통한 스파이로 접합 및 N-헤테로고리 화합물의 새로운 합성법 개발 연구”으로 총 8장으로 구성되어 있다. 이와 관련하여, 본 논문은 균질성 및 이질성 촉매를 사용하여 스파이로 접합, 폴리 헤테로고리 및 N- 헤테로고리 뼈대의 합성을위한 다성분반응의 응용을 다룬다. 이 관점에서 우리는 주로 기존의 산 / 염기 시스템과 연관된 환경적 위험을 줄이기 위한 훌륭한 재사용 가능 촉매를 찾는 데 중점을 두었습니다. 또한 다양한 이질성 촉매들을 제조, 다양하고 유용한 이질성 뼈대의 합성이 스크리닝 및 이용되었다. Knoevenagel 반응, Mannich 반응, Michael 반응 및 고리화 반응을 통해 일련의 다양한 스파이로 융합, 폴리 헤테로고리 및 N- 헤테로 고리 구조를 우수한 수율로 용이하게 제조 하였다. 더욱이, 이러한 방법론들이 다양한 기능을 갖는 핵심 구조를 도입하기 위하여 개발되었다.
- Issued Date
- 2020
- Awarded Date
- 2020. 2
- Type
- Dissertation
- Publisher
- 부경대학교
- Affiliation
- Pukyong National University , Graduate School
- Department
- 대학원 융합디스플레이공학과
- Advisor
- YEONTAEJEONG
- Table Of Contents
- Development of New Methodologies for the Synthesis of Spiro-Fused and N-heterocyclic Compounds throughMulticomponentReaction 1
I.I Introduction 1
I.II Aim of this thesis 3
I.III References 5
Chapter 1. A novel three-component method for the synthesis of spiro [chromeno [4',3':4,5] pyrimido[1,2-b]indazole-7,3'-indoline]-2',6(9H)-dione 6
1.1. Introduction 6
1.2. Result and Discussion 8
1.3. Conclusion 14
1.4. Experimental 14
1.4.1 Materials and methods 14
1.4.2. Typical experimental procedure for the synthesis of spiro [chromeno [4',3':4,5]pyrimido[1,2-b]indazole-7,3'-indoline]-2',6(9H)-dione 14
1.4.3. Spectral Characterization data 15
1.5. References 31
Chapter 2. Silica-supported tungstic acid (STA): A recyclable catalyst for the synthesis of 1H-indazolo [1,2-b]phthalazine-trione and spiro-triazolo[1,2-a]indazole-tetraone derivatives under solvent-free condition 33
2.1 Introduction 33
2.2. Result and Discussion 35
2.3. Conclusion 43
2.4. Experimental 43
2.4.1 Materials and methods 43
2.4.2. General procedure for the synthesis of 13-(4-chlorophenyl)-3,3-dimethyl-2,3,4,13-tetrahydro-1H-indazolo[1,2-b]phthalazine-1,6,11-trione (4a) 44
2.4.3. Spectral Characterization data 44
2.5. References 63
Chapter 3. A highly efficient and recyclable silica-supported tungstic acid (STA) catalyst for the synthesis of pyrano[3,2-c]chromen-5-ones under solvent-free conditions 66
3.1. Introduction 66
3.2. Result and Discussion 69
3.3. Conclusion 76
3.4. Experimental 76
3.4.1. Materials and methods 76
3.4.2. General procedure for the synthesis of 4-(4-methoxyphenyl)-2-(methylamino)-3-nitro-4H,5H-pyrano [3,2-c]chromen-5-one (4a) 76
3.4.3. Spectral Characterization data 77
3.5. References 96
Chapter 4. Application of p-TSA in the one-pot synthesis of N-methyl-3-nitro-aryl-benzo[4,5]imidazo[1,2-a]pyrimidin-2-amine 99
4.1. Introduction 99
4.2. Result and Discussion 101
4.3. Conclusion 107
4.4. Experimental 107
4.4.1 Materials and methods 107
4.4.2. General procedure for the synthesis of 4-(4-chlorophenyl)-N-methyl-3-nitro-4,10-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-2-amine (4a) 107
4.4.3. Spectral Characterization data 108
4.5. References 124
Chapter 5. A metal-free C–C/C–O bond formation for the synthesis of 2-amino-5-oxo-4-aryl-4H,5H-pyrano[3,2-c]chromene-3-carboxa-mide catalyzed by polystyrene supported p-toluenesulfonic acid (PS-PTSA) 127
5.1. Introduction 127
5.2. Result and Discussion 130
5.3. Conclusion 137
5.4. Experimental 138
5.4.1 Materials and methods 138
5.4.2. Synthesis of 2-amino-4-(4-chlorophenyl)-5-oxo-4H,5H-pyrano[3,2-c]chromene-3carboxamide (4a) 138
5.4.3. Spectral Characterization data 138
5.5. References 156
Chapter 6. Indium(III) chloride catalyzed synthesis of novel 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and 1H-pyrazolo[1,2-a]pyridazine-5,8-diones under solvent-free condition 160
6.1. Introduction 160
6.2. Result and Discussion 163
6.3. Conclusion 171
6.4. Experimental 171
6.4.1 Materials and methods 171
6.4.2. General Procedure for the Synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones and 1H-pyrazolo-[1,2-a]pyridazine-5,8-diones (4a) 171
6.4.3. Spectral Characterization data 172
6.5. References 197
Chapter 7. An efficient protocol for synthesis of novel polyheterocyclic chromeno pyrimid[1,2-b indazolone derivatives using [Et3NH][HSO4] as a reusable catalyst under solvent-free conditions 201
7.1. Introduction 201
7.2. Result and Discussion 203
7.3. Conclusion 210
7.4. Experimental 210
7.4.1 Materials and methods 210
7.4.2. General procedure for the synthesis of 7-(4-chlorophenyl)-7,14-dihydro-6H-chromeno [4',3':4,5]pyrimido[1,2-b]indazol-6-one (4a) 211
7.4.3. Spectral Characterization data 211
7.5. References 230
Chapter 8. L-proline catalyzed unprecedented synthesis of novel naphtho-bis[1,3]oxazines under solvent-free conditions 232
8.1. Introduction 232
8.2. Result and Discussion 235
8.3. Conclusion 242
8.4. Experimental 243
8.4.1 Materials and methods 243
8.4.2. General procedure for the synthesis of 3,10-diphenyl-2,3,4,9,10,11-hexahydro naphtho[1,2-e:4,3-e']bis[1,3]oxazine (4a) 243
8.4.3. Spectral Characterization data 243
8.5. References 264
Chapter 9 267
9.1 Summary 267
9.2 List of publications from the present study 268
- Degree
- Doctor
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