Manganese(III) acetate mediated oxidative radical cyclizations of α-substituted N-[2-(phenylethynyl)phenyl]acetamides

Che Ping Chuang, Yan Jhu Chen

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

An effective method for the synthesis of 3,4-disubstituted quinolin-2(1H)-ones was reported. α-Carbonylalkyl radical, produced by the manganese(III) acetate oxidation of α-substituted N-[2-(phenylethynyl)phenyl]acetamides, undergoes a 6-exo-dig cyclization onto the C-C triple bond efficiently and 3,4-disubstituted quinolin-2(1H)-ones were produced. Heterocyclic substrates could also be used to generate the corresponding quinolin-2(1H)-ones smoothly. A variety of functional groups, including methoxycarbonyl, cyano, diethoxyphosphoryl and benzoyl groups, are compatible with the reaction conditions. Under Mn(II)/Co(II)/O2 conditions, the formation of these quinolin-2(1H)-ones could also be achieved from the corresponding N-[2-(phenylethynyl)phenyl]acetamides and a catalytic amount of manganese(II) acetate was used.

Original languageEnglish
Pages (from-to)1911-1918
Number of pages8
JournalTetrahedron
Volume72
Issue number16
DOIs
Publication statusPublished - 2016 Apr 21

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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