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Title: One-pot synthesis of highly substituted N-fused heteroaromatic bicycles from azole aldehydes.

Authors: Outlaw, Victor K; d'Andrea, Felipe B; Townsend, Craig A

Published In Org Lett, (2015 Apr 17)

Abstract: An efficient route to substituted N-fused aromatic heterocycles, including indolizines, imidazo[1,2-a]pyridines, and imidazo[1,5-a]pyridines from azole aldehydes, is reported. Wittig olefination of the aldehydes with fumaronitrile and triethylphosphine affords predominantly E-alkenes that undergo rapid cyclization upon treatment with a mild base. Substituent control of the 1-, 2-, and 3-positions of the resulting heteroaromatic bicycles is shown. Alternatively, the isolable E-alkene undergoes selective alkylation with electrophiles, followed by in situ annulation to indolizines additionally substituted at the 6-position.

PubMed ID: 25815402 Exiting the NIEHS site

MeSH Terms: No MeSH terms associated with this publication

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