A general synthesis of N-substituted 1,4-benzoxazine- and 1,4-benzothiazine-2-carboxylates via copper-catalyzed intramolecular amination of arylbromides

Ferdinand Melkonyan, Artiom Topolyan, Alexander Karchava*, Marina Yurovskaya

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

Starting from ortho-bromosubstituted phenoxyacetates or (phenythio)acetates and primary amines, various N-substituted 4H-1,4-benzoxazine- and 4H-1,4-benzothiazine-2-carboxylates were synthesized in moderate to high yields by using a Cu(I)-catalyzed Ullmann-type cyclization as a key step. The method is simple to operate, tolerates many functional groups and does not require any additives.

Original languageEnglish (US)
Pages (from-to)6826-6832
Number of pages7
JournalTetrahedron
Volume67
Issue number36
DOIs
StatePublished - Sep 9 2011

Keywords

  • 1,4-Benzothiazine
  • 1,4-Benzoxazine
  • Copper-catalyzed reactions
  • Cyclization
  • Heterocycles
  • Ullmann amination reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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