Synthesis of 1,2,4-Triazol-3-imines via Selective Stepwise Cycloaddition of Nitrile Imines with Organo-cyanamides

Pallavi Sharma; Shreesha V Bhat; M R Ranga Prabhath; Andrew Molino; Elisa Nauha; David J D Wilson; John E Moses

doi:10.1021/acs.orglett.8b01673

Synthesis of 1,2,4-Triazol-3-imines via Selective Stepwise Cycloaddition of Nitrile Imines with Organo-cyanamides

Org Lett. 2018 Jul 20;20(14):4263-4266. doi: 10.1021/acs.orglett.8b01673. Epub 2018 Jun 28.

Authors

Pallavi Sharma^{1

2}, Shreesha V Bhat², M R Ranga Prabhath², Andrew Molino¹, Elisa Nauha², David J D Wilson¹, John E Moses¹

Affiliations

¹ La Trobe Institute for Molecular Science , La Trobe University , Bundoora , VIC 3086 , Australia.
² School of Chemistry, Joseph Banks Laboratory , University of Lincoln , Lincoln , LN6 7DL , U.K.

PMID: 29952574
DOI: 10.1021/acs.orglett.8b01673

Abstract

A convenient method for the synthesis of 1,2,4-triazol-3-imines through a selective, formal, 1,3-dipolar cycloaddition of organo-cyanamide ions with nitrile imine dipoles is reported. Hydrolysis of the 1,2,4-triazol-3-imines yields the corresponding 1,2,4-triazol-5-ones. A stepwise mechanism, supported by DFT calculations, is invoked to explain the reaction selectivity.

Publication types

Research Support, Non-U.S. Gov't