Organic amine-mediated free-radical carbocyclization reactions of 2,2,2-trihalogeno-substituted: N -(2-alkynylphenyl)acetamides

Tsung Han Chuang, Che-Ping Chuang

Research output: Contribution to journalArticle

Abstract

An efficient method for the synthesis of 3-halogeno-substituted 4-benzoylquinolin-2-(1H)-ones from N-(2-alkynylphenyl)-substituted trihaloacetamides has been developed, in which organic amines (TNPA and DIEA) act as the electron donors. In this carbocyclization reaction, a new C-C bond formation occurred regioselectively via a 6-exo-dig radical cyclization. A variety of useful functional groups are compatible with the reaction conditions. In this process, readily removable organic amines were employed and no heavy metal catalysts were required.

Original languageEnglish
Pages (from-to)7265-7273
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume16
Issue number39
DOIs
Publication statusPublished - 2018 Jan 1

Fingerprint

Acetamides
Free radical reactions
free radicals
Free Radicals
Amines
amines
Cyclization
heavy metals
Heavy Metals
Functional groups
Electrons
catalysts
Catalysts
synthesis
electrons

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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abstract = "An efficient method for the synthesis of 3-halogeno-substituted 4-benzoylquinolin-2-(1H)-ones from N-(2-alkynylphenyl)-substituted trihaloacetamides has been developed, in which organic amines (TNPA and DIEA) act as the electron donors. In this carbocyclization reaction, a new C-C bond formation occurred regioselectively via a 6-exo-dig radical cyclization. A variety of useful functional groups are compatible with the reaction conditions. In this process, readily removable organic amines were employed and no heavy metal catalysts were required.",
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Organic amine-mediated free-radical carbocyclization reactions of 2,2,2-trihalogeno-substituted : N -(2-alkynylphenyl)acetamides. / Chuang, Tsung Han; Chuang, Che-Ping.

In: Organic and Biomolecular Chemistry, Vol. 16, No. 39, 01.01.2018, p. 7265-7273.

Research output: Contribution to journalArticle

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