Three-Component Bicyclization Leading to Densely Functionalized Pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines

Wen Juan Hao; Peng Zhou; Fei Yue Wu; Bo Jiang; Shu Jiang Tu; Guigen Li

doi:10.1002/ejoc.201600163

Three-Component Bicyclization Leading to Densely Functionalized Pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines

Wen Juan Hao, Peng Zhou, Fei Yue Wu, Bo Jiang, Shu Jiang Tu, Guigen Li

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

Abstract

A three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines from readily accessible aryl aldehydes, α-thiocyanate ketones, and pyrazol-5-amines was established. The reaction pathway involves a nucleophilic addition/5-exo-trig/6-endo-trig bicyclization sequence that results in continuous multiple bond-forming events, including the formation of C-N and C-C bonds, to give high levels of molecular complexity.

Original language	English
Pages (from-to)	1968-1971
Number of pages	4
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	11
DOIs	https://doi.org/10.1002/ejoc.201600163
State	Published - Apr 1 2016

Keywords

Cyclization
Fused-ring systems
Microwave chemistry
Multicomponent reactions
Polycycles

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title = "Three-Component Bicyclization Leading to Densely Functionalized Pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines",

abstract = "A three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines from readily accessible aryl aldehydes, α-thiocyanate ketones, and pyrazol-5-amines was established. The reaction pathway involves a nucleophilic addition/5-exo-trig/6-endo-trig bicyclization sequence that results in continuous multiple bond-forming events, including the formation of C-N and C-C bonds, to give high levels of molecular complexity.",

keywords = "Cyclization, Fused-ring systems, Microwave chemistry, Multicomponent reactions, Polycycles",

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AU - Jiang, Bo

AU - Tu, Shu Jiang

AU - Li, Guigen

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AB - A three-component bicyclization strategy for the efficient synthesis of densely functionalized pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidines from readily accessible aryl aldehydes, α-thiocyanate ketones, and pyrazol-5-amines was established. The reaction pathway involves a nucleophilic addition/5-exo-trig/6-endo-trig bicyclization sequence that results in continuous multiple bond-forming events, including the formation of C-N and C-C bonds, to give high levels of molecular complexity.

KW - Cyclization

KW - Fused-ring systems

KW - Microwave chemistry

KW - Multicomponent reactions

KW - Polycycles

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