Synthesis of N-heterocycles containing 1,5-disubstituted-1H-tetrazole via post-Ugi-azide reaction

Mol Divers. 2020 Aug;24(3):841-853. doi: 10.1007/s11030-019-09972-1. Epub 2019 Jun 20.

Abstract

Ugi-azide four-component reaction (UA-4CR) as development on Ugi four-component reaction (U-4CR) is the condensation reaction involving an aldehyde, an amine, an isocyanide, and an azide source. Nowadays, UA-4CR has been employed for the efficient and facile production of 1,5-disubstituted-1H-tetrazoles (1,5-DS-1H-Ts). Interestingly, the combination of 1,5-DS-1H-Ts with suitable post-transformations in a tandem manner results in the construction of various classes of heterocyclic compounds bearing 1,5-DS-1H-T moiety. This review aims to provide the application of diverse post-Ugi-azide reaction in the preparation of different N-heterocyclic compounds bearing 1,5-DS-1H-T such as substituted and fused 1,5-DS-1H-Ts.

Keywords: 1,5-DS-1H-Ts; 1,5-Disubstituted-1H-tetrazoles; Isocyanides; MCRs; Multicomponent reaction; Post-Ugi-azide reaction.

Publication types

  • Review

MeSH terms

  • Azides / chemistry*
  • Chemistry Techniques, Synthetic / methods*
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry*
  • Nitrogen / chemistry*
  • Tetrazoles / chemistry*

Substances

  • Azides
  • Heterocyclic Compounds
  • Tetrazoles
  • Nitrogen