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

15 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

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of 2-Substituted Quinolines from 2-Aminostyryl Ketones Using Iodide as a Catalyst'. Together they form a unique fingerprint.

  • Cite this