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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 and John E. Moses*

*La Trobe Institute for Molecular Science, La Trobe University, Bundoora, VIC 3086, Australia, Email: p.sharmalatrobe.edu.au, j.moseslatrobe.edu.au

P. Sharma, S. B. Bhat, M. R. R. Prabhath, A. Molino, E. Nauha, D. J. D. Wilson, J. E. Moses, Org. Lett., 2018, 20, 4263-4266.

DOI: 10.1021/acs.orglett.8b01673 (free Supporting Information)


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Abstract

A selective, formal, 1,3-dipolar cycloaddition of organo-cyanamide ions with nitrile imine dipoles provides 1,2,4-triazol-3-imines. Hydrolysis of the 1,2,4-triazol-3-imines yields the corresponding 1,2,4-triazol-5-ones.

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Key Words

N-heterocycles


ID: J54-Y2018