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

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.

SUBMITTER: Outlaw VK

PROVIDER: S-EPMC4500639 | biostudies-literature | 2015 Apr

REPOSITORIES: biostudies-literature

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

Outlaw Victor K VK d'Andrea Felipe B FB Townsend Craig A CA

Organic letters 20150327 8

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 se ...[more]

PMID: 25815402

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