Base-Promoted Carbocyclization Reactions of α-Substituted N-(2-Alkynylphenyl)acetamides

Yan Jhu Chen, Che Ping Chuang

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

A synthetic method for highly functionalized quinolin-2(1H)-ones has been developed. The copper(II) chloride-catalyzed aerobic oxidative carbocyclization reactions of α-substituted N-[2-(phenylethynyl)phenyl]acetamides, via the Conia-ene-type intramolecular carbocupration onto the alkynyl moiety, produced 3,4-difunctionalized quinolin-2(1H)-ones. In the absence of copper(II) chloride, these α-substituted acetamides undergo base-promoted nucleophilic 6-exo-dig carbocyclization to generate 3-functionalized quinolin-2(1H)-ones. Several useful functional groups including benzoyl, alkanoyl, diethoxyphosporyl, cyano, and methoxycarbonyl groups are compatible with the reaction conditions. α-Substituted N-(2-ethynylphenyl)acetamides bearing a terminal C≡C bond could also be used to generate the corresponding 4-methyl-substituted quinolin-2(1H)-ones smoothly.

Original languageEnglish
Pages (from-to)3603-3617
Number of pages15
JournalSynthesis (Germany)
Volume48
Issue number20
DOIs
Publication statusPublished - 2016 Oct 17

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Base-Promoted Carbocyclization Reactions of α-Substituted N-(2-Alkynylphenyl)acetamides'. Together they form a unique fingerprint.

Cite this