Four-Component Bicyclization Approaches to Skeletally Diverse Pyrazolo[3,4-b]pyridine Derivatives

被引：69

作者：

Tu, Xing-Jun ^{[1
]}

Hao, Wen-Juan ^{[1
]}

Ye, Qin ^{[1
]}

Wang, Shuang-Shuang ^{[1
]}

Jiang, Bo ^{[1
]}

Li, Guigen ^{[2
,3
]}

Tu, Shu-Jiang ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Jiangsu Key Lab Green Synthet Chem Funct Mat, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China

[2] Nanjing Univ, Inst Chem & Biomed Sci, Nanjing 210093, Jiangsu, Peoples R China

[3] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 22期

基金：

美国国家卫生研究院;

关键词：

PYRIDINE MONOTERPENE ALKALOIDS; DIELS-ALDER REACTION; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; STEREOSELECTIVE-SYNTHESIS; BIOLOGICAL EVALUATION; INHIBITORS; ACCESS; HETEROANNULATION; CYCLOADDITION;

D O I：

10.1021/jo502096t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel four-component bicyclization strategy has been established, allowing a flexible and practical approach to 37 examples of multicyclic pyrazolo[3,4-b]pyridines from low-cost and readily accessible arylglyoxals, pyrazol-5-amines, aromatic amines, 4-hydroxy-6-methyl-2H-pyran-2-one, and cyclohexane-1,3-diones. The polysubstituted cyclopenta[d]pyrazolo[3,4-b]pyridines were stereoselectively synthesized through a microwave-assisted special [3+2+1]/[3+2] bicyclization with good control of the spatial configuration of exocyclic double bonds. The novel [3+2+1]/[2+2+1] bicyclization resulted in 17 examples of unreported pyrazolo[3,4-b]pyrrolo[4,3,2-de]quinolones. Reasonable mechanisms for forming two new types of multicyclic pyrazolo[3,4-b]pyridines are also proposed.

引用

页码：11110 / 11118

页数：9

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