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Copper-Catalyzed Synthesis of Trinuclear N-Fused Hybrid Scaffolds by Double C(sp2)–N Bond Formation between 2-(2-Bromoaryl)indoles and 2-Aminoazoles

  • Thi Duyen Diep
  • , Pham Duy Quang Dao
  • , Son Long Ho
  • , Chan Sik Cho
  • Kyungpook National University

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

2-(2-Bromoaryl)indoles react with 2-aminoazoles by microwave irradiation in DMF in the presence of a catalytic amount of CuI and a base to produce trinuclear N-fused hybrid scaffolds, benzo[4,5]imidazo[1,2-a]indolo[1,2-c]quinazolines and imidazo[1,2-a]indolo[1,2-c]quinazolines in moderate to good yields. The reaction seems to proceed via copper-catalyzed C(sp2)-N coupling and subsequent intramolecular cyclocondensation accompanied by ammonia evolution. Complete regioselective C–N cyclization is observed with the reaction of 2-(2-bromophenyl)indole with 2-aminoazoles.

Original languageEnglish
Pages (from-to)2807-2812
Number of pages6
JournalEuropean Journal of Organic Chemistry
Volume2020
Issue number19
DOIs
StatePublished - 22 May 2020

Keywords

  • 2-Aminoazoles
  • Cyclization
  • C–N bond formation
  • Homogeneous catalysis
  • Nitrogen heterocycles

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