Premium
A Modular Synthesis of Polysubstituted Indolizines
Author(s) -
Kucukdisli Murat,
Opatz Till
Publication year - 2012
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.201200424
Subject(s) - indolizine , chemistry , pyridine , alkylation , pyridinium , organic chemistry , cyanohydrin , combinatorial chemistry , catalysis
The N‐alkylation of pyridines with cyanohydrin triflates or α‐halonitriles furnishes 1‐(1‐cyanoalkyl)pyridinium salts that can react with nitroolefins under basic conditions to furnish polysubstituted indolizines. Overall, the indolizine core can be constructed from a pyridine, two aldehydes, and a nitroalkane, and no undesired functional groups remain in the products. When bromoacetonitrile was used for the N‐alkylation, indolizine‐3‐carbonitriles were obtained instead. The pyridine component may be replaced by other azines, giving rise to related heterocyclic systems.