Synthesis of 2-Substituted Quinolines from 2-Aminostyryl Ketones Using Iodide as a Catalyst

So Young Lee, Jiye Jeon, Cheol-Hong Cheon

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

A new protocol for the synthesis of 2-substituted quinolines from 2-aminostyryl ketones has been developed using iodide as a nucleophilic catalyst. Conjugate addition of iodide to 2-aminostyryl ketones yielded the corresponding β-iodoketones, which could have a conformation where the amino and carbonyl groups are proximal through free rotation about the Cα-Cβ single bond. Subsequent condensation between the amino and carbonyl groups followed by elimination of hydrogen iodide provided the corresponding quinolines, with regeneration of the iodide catalyst.

Original languageEnglish
Pages (from-to)5177-5186
Number of pages10
JournalJournal of Organic Chemistry
Volume83
Issue number9
DOIs
Publication statusPublished - 2018 May 4

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Quinolines
Iodides
Ketones
Catalysts
Conformations
Regeneration
Condensation

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of 2-Substituted Quinolines from 2-Aminostyryl Ketones Using Iodide as a Catalyst. / Lee, So Young; Jeon, Jiye; Cheon, Cheol-Hong.

In: Journal of Organic Chemistry, Vol. 83, No. 9, 04.05.2018, p. 5177-5186.

Research output: Contribution to journalArticle

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