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

Youngeun Jung; Ikyon Kim

doi:10.1021/acs.orglett.5b02331

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

Youngeun Jung, Ikyon Kim

Department of Pharmacy

Research output: Contribution to journal › Article › peer-review

29 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4600-4603
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.5b02331
Publication status	Published - 2015 Sep 18

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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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N2 - 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.

AB - 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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