Silver-Catalyzed Cascade Cyclization of Amino- NH-1,2,3-Triazoles with 2-Alkynylbenzaldehydes: An Access to Pentacyclic Fused Triazoles

Molecules. 2022 Nov 4;27(21):7567. doi: 10.3390/molecules27217567.

Abstract

An operationally simple Ag(I)-catalyzed approach for the synthesis of isoquinoline and quinazoline fused 1,2,3-triazoles was developed by a condensation and amination cyclization cascade of amino-NH-1,2,3-triazoles with 2-alkynylbenzaldehydes involving three new C-N bond formations in one manipulation, in which the group of -NH of the triazole ring serves as a nucleophile to form the quinazoline skeleton. The efficient protocol can be applied to a variety of substrates containing a range of functional groups, delivering novel pentacyclic fused 1,2,3-triazoles in good-to-excellent yields.

Keywords: cascade; cyclizations; fused 1,2,3-triazoles; isoquinoline; quinazoline.

MeSH terms

  • Catalysis
  • Cyclization
  • Molecular Structure
  • Quinazolines
  • Silver*
  • Triazoles* / chemistry

Substances

  • Triazoles
  • Silver
  • Quinazolines