Selective Synthesis of New Tetracyclic Coumarin-fused Pyrazolo[3,4-b]pyridines and Pyrazolo[3,4-b]pyridin-6(7H)-ones

被引：12

作者：

Liu, Meilin ^{[1
]}

Yin, Guodong ^{[1
]}

Zhu, Can ^{[1
]}

Yao, Chaochao ^{[1
]}

机构：

[1] Hubei Normal Univ, Hubei Key Lab Pollutant Anal & Reuse Technol, Hubei Collaborat Innovat Ctr Rare Met Chem, Huangshi 435002, Peoples R China

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2016年 / 53卷 / 05期

关键词：

MULTICOMPONENT REACTIONS; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; DERIVATIVES; INHIBITORS; POTENT;

D O I：

10.1002/jhet.2473

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A three-component reaction for the synthesis of new coumarin-fused tetracyclic system from 4-hydroxycoumarin, aldehydes, and 5-aminopyrazoles/5-aminoisoxazole is described. In the presence of acetic acid, 4,7-dihydro-1H-pyrazolo[3,4-b]pyridines (4) and pyrazolo[ 3,4-b] pyridines (5) were obtained in acetonitrile and dimethylsulfoxide medium, respectively. The reaction gave rise to 4,5-dihydro-1H-pyrazolo[ 3,4-b] pyridin-6(7H)-ones (6) in acetic acid-ethanol combination system, which involved the C-O bond cleavage. 4-Hydroxy-6-methyl-2H-pyran-2-one and acenaphthylene-1,2-dione were also examined, affording the corresponding C-O bond cleavage products. Mechanism indicates that the reaction is reversible in acetic acid-ethanol combination system.

引用

页码：1617 / 1625

页数：9

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