Deformylative Intramolecular Hydroarylation

Synthesis of Benzo[e]pyrido[1,2-a]indoles

Youngeun Jung, Ikyon Kim

Research output: Contribution to journalArticle

17 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 languageEnglish
Pages (from-to)4600-4603
Number of pages4
JournalOrganic Letters
Volume17
Issue number18
DOIs
Publication statusPublished - 2015 Sep 18

Fingerprint

Indoles
Alkynes
indoles
alkynes
Indolizines
Bearings (structural)
metathesis
Cyclization
synthesis
Catalysis
catalysis
acids
Acids
products

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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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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Deformylative Intramolecular Hydroarylation : Synthesis of Benzo[e]pyrido[1,2-a]indoles. / Jung, Youngeun; Kim, Ikyon.

In: Organic Letters, Vol. 17, No. 18, 18.09.2015, p. 4600-4603.

Research output: Contribution to journalArticle

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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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