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Synthesis of Oxadiazol-5-imines via the Cyclizative Capture of in Situ Generated Cyanamide Ions and Nitrile Oxides

Shreesha V. Bhat, David Robinson John E. Moses* and Pallavi Sharma*

*School of Chemistry, University of Lincoln, Lincoln, LN6 7DL; School of Chemistry, University Park, University of Nottingham, Nottingham, NG7 2RD, U.K., Email: psharmalincoln.ac.uk, john.mosesnottingham.ac.uk

S. V. Bhat, D. Robinson, J. E. Moses, P. Sharma, Org. Lett., 2016, 18, 1100-1103.

DOI: 10.1021/acs.orglett.6b00203 (free Supporting Information)


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Abstract

An unprecedented intermolecular cyclizative capture of the cyanamide anion and several nitrile oxides enables the synthesis of 1,2,4-oxadiazol-5(4H)-imines. Treatment of the imine products with concd. HCl furnishes 1,2,4-oxadiazol-5(4H)-ones.

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Key Words

N-heterocycles


ID: J54-Y2016