Four-component bicyclization approaches to skeletally diverse pyrazolo[3,4- b ]pyridine derivatives

Xing Jun Tu, Wen Juan Hao, Qin Ye, Shuang Shuang Wang, Bo Jiang, Guigen Li, Shu Jiang Tu

Research output: Contribution to journalArticle

39 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)11110-11118
Number of pages9
JournalJournal of Organic Chemistry
Volume79
Issue number22
DOIs
StatePublished - Nov 21 2014

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