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Three‐Component Bicyclization Leading to Densely Functionalized Pyrazolo[3,4‐ d ]thiazolo[3,2‐ a ]pyrimidines
Author(s) -
Hao WenJuan,
Zhou Peng,
Wu FeiYue,
Jiang Bo,
Tu ShuJiang,
Li Guigen
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600163
Subject(s) - chemistry , aryl , component (thermodynamics) , nucleophile , combinatorial chemistry , stereochemistry , thiocyanate , sequence (biology) , organic chemistry , biochemistry , catalysis , alkyl , physics , thermodynamics
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.