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Org Lett. 2015 Sep 18;17(18):4600-3. doi: 10.1021/acs.orglett.5b02331. Epub 2015 Sep 08.

Deformylative Intramolecular Hydroarylation: Synthesis of Benzo[e]pyrido[1,2-a]indoles.

Organic letters

Youngeun Jung, Ikyon Kim

Affiliations

  1. College of Pharmacy and Yonsei Institute of Pharmaceutical Sciences, Yonsei University , 85 Songdogwahak-ro, Yeonsu-gu, Incheon 406-840, Republic of Korea.

PMID: 26345614 DOI: 10.1021/acs.orglett.5b02331

Abstract

Attempted cyclization of indolizines bearing both formyl and alkyne groups under acid catalysis provided benzo[e]pyrido[1,2-a]indoles with an aryl substituent at the C6 position as major products, along with the expected C5-acylated benzo[e]pyrido[1,2-a]indoles as minor ones, which resulted from preferential deformylative intramolecular hydroarylation instead of intended alkyne-carbonyl metathesis.

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