臺灣博碩士論文加值系統

使用5-(2-chloroacetylamino)pyrazoles和PBr3在formamide溶液中，經過一鍋化之多步反應，成功得出一系列6-[(formyl)methyl]- 1H-pyrazolo[3,4-d]pyrimidine產物，產率為73–92%。依據實驗結果，此一鍋多步反應涉及Vilsmeier-Haack反應、Morgan-Walls反應、連續消除、取代反應及水解反應等步驟。

A new one-pot multicomponent reaction was successfully developed as a key strategy for the synthesis of 6-[(formyl)methyl]-1H-pyrazolo[3,4-d]- pyrimidine compounds from 5-(2-chloroacetylamino)pyrazoles with formamide in presence of PBr3. Under the reliable condition, the tandem multicomponent reactions involving Vilsmeier-Haack reaction, Morgan-Walls reaction, sequential elimination, substitution reaction, and final hydrolysis reaction efficiently afforded formylmethylpyrazolo[3,4-d]pyrimidine products in good yields (73–92%).

Contents I
Chart List III
Chart of Figure III
Chart of Scheme VII
Chart of Table VIII
Abbreviations IX
中文摘要 X
Abstract XI
Chapter 1. Introduction 1
1.1 One-pot Reaction 1
1.2 Preparation of Vilsmeier-Type Reagents 2
1.3 Application of Vilsmeier-Type Reaction 3
1.4 Bioactivity of Pyrazolopyrimidine Derivatives 6
Chapter 2. Research Approach 8
Chapter 3. Results & Discussion 9
3.1 Chemistry 9
3.1.1 Study of Coupling Agents 9
3.1.2 Study of Leaving Group Effect 11
3.1.3 Synthesis of 6-[(Formyl)methyl]-1H-pyrazolo-[3,4-d]- pyrimidines 13
3.1.4 Study of Mechanism 17
3.2 Bioactivity 20
Chapter 4. Conclusions 24
Chapter 5. Experimental Section 26
5.1 General Procedure 26
5.1.1 Investigation of New Vilsmeier-Type Reaction Using 5-(2-Chloroacetylamino)pyrazoles with Formamide 26
5.2 Cell Lines 42
5.3 Growth Inhibition Assay 43
Reference 44

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