Selective synthesis of pyrazolo[3,4-d]pyrimidine, N-(1H-pyrazol-5-yl) formamide, or N-(1H-pyrazol-5-yl)formamidine derivatives from N-1-substituted-5-aminopyrazoles with new Vilsmeier-type reagents

被引：28

作者：

Chang, Chun-Hsi ^{[1
]}

Tsai, Henry J. ^{[2
]}

Huang, Yu-Ying ^{[1
]}

Lin, Hui-Yi ^{[3
]}

Wang, Li-Ya ^{[4
]}

Wu, Tian-Shung ^{[3
]}

Wong, Fung Fuh ^{[1
]}

机构：

[1] China Med Univ, Grad Inst Pharmaceut Chem, Taichung 40402, Taiwan

[2] Asia Univ, Dept Hlth & Nutr Biotechnol, Taichung Cty 413, Taiwan

[3] China Med Univ, Sch Pharm, Taichung 40402, Taiwan

[4] China Med Univ, Ph D Program Canc Biol & Drug Discovery, Taichung 40402, Taiwan

来源：

TETRAHEDRON | 2013年 / 69卷 / 04期

关键词：

Vilsmeier reaction; 5-Aminopyrazoles; Pyrazolo[3,4-d]pyrimidine; Formamidine; Formamide; ONE-POT SYNTHESIS; NUCLEOPHILIC-SUBSTITUTION; EFFICIENT SYNTHESIS; (ALKOXYMETHYLENE)DIMETHYLAMMONIUM CHLORIDE; CYCLODEHYDRATION REACTION; REGIOSELECTIVE SYNTHESIS; CONVENIENT PROCEDURE; FACILE SYNTHESIS; HAACK REACTION; CYCLIZATION;

D O I：

10.1016/j.tet.2012.11.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Various halomethyleniminium salts as novel Vilsmeier agents were synthesized from formamide or N-methylformamide with POCl3. Treatment of N-1-substituted-aminopyrazoles including N-1-phenyl-5-aminopyrazoles, N-1-(2-pyridinyl)-5-aminopyrazoles, and N-1-(2-quinolinyl)-5-aminopyrazoles with these agents gave the corresponding pyrazolo[3,4-d]pyrimidine,N-(1H-pyrazol-5-yl)formamide, or N-(1H-pyrazol-5-yl)formamidine. The reaction was different from the traditional Vilsmeier-type reaction and the plausible reactive pathways were proposed for the unexpected result. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1378 / 1386

页数：9

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