Jump to main content
Jump to site search


An efficient synthesis of 4,5-disubstituted-2H-1,2,3-triazoles from nitroallylic derivatives via a cycloaddition–denitration process

Author affiliations

Abstract

A metal-free convenient synthesis of 4,5-disubstituted N-unsubstituted 1,2,3-triazoles via a cycloaddition–denitration process has been described. A variety of readily available nitroallylic alcohols were reacted smoothly with sodium azide in the presence of p-toluenesulfonic acid (p-TsOH) to form synthetically viable triazolylacetates in good to high yields. Additionally, the nitroallylic acetates and sulfones were converted into structurally-modifiable triazolylazides and sulfone derived triazoles, respectively, in moderate to good yields. The present protocol is operationally simple, tolerates a broad range of functional groups and is also reliable in the case of a gram scale reaction under optimised reaction conditions. A practically-straightforward gram scale reaction for the synthesis of triazole directly from β-nitrostyrene via a sequential one-pot Morita–Baylis–Hillman and cycloaddition reactions has been achieved.

Graphical abstract: An efficient synthesis of 4,5-disubstituted-2H-1,2,3-triazoles from nitroallylic derivatives via a cycloaddition–denitration process

Back to tab navigation

Supplementary files

Publication details

The article was received on 31 Aug 2017, accepted on 03 Dec 2017 and first published on 04 Dec 2017


Article type: Paper
DOI: 10.1039/C7NJ03292G
Citation: New J. Chem., 2018, Advance Article
  •   Request permissions

    An efficient synthesis of 4,5-disubstituted-2H-1,2,3-triazoles from nitroallylic derivatives via a cycloaddition–denitration process

    R. Jannapu Reddy, Md. Waheed, T. Karthik and A. Shankar, New J. Chem., 2018, Advance Article , DOI: 10.1039/C7NJ03292G

Search articles by author

Spotlight

Advertisements