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

Sharma, P., Bhat, S. V., Prabhath, M. R. R., Molino, A., Nauha, E., Wilson, D. J. D., Moses, J. E. (July 2018) Synthesis of 1,2,4-Triazol-3-imines via Selective Stepwise Cycloaddition of Nitrile Imines with Organo-cyanamides. Org Lett, 20 (14). pp. 4263-4266. ISSN 1523-7052

URL: https://pubmed.ncbi.nlm.nih.gov/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.

Item Type: Paper
CSHL Authors:
Communities: CSHL labs > Moses lab
Depositing User: Matthew Dunn
Date: 20 July 2018
Date Deposited: 08 Jan 2021 17:30
Last Modified: 08 Jan 2021 17:30
Related URLs:
URI: https://repository.cshl.edu/id/eprint/39581

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