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A new and facile synthesis of N-Benzyl-N’-acylureas via reaction of dibenzoylhydrazine carboxamide and benzylamines

Valipour, M., Chippindale, A. M., Kouzeli, A. and Irannejad, H. (2021) A new and facile synthesis of N-Benzyl-N’-acylureas via reaction of dibenzoylhydrazine carboxamide and benzylamines. Synthetic Communications, 51 (19). pp. 3004-3012. ISSN 0039-7911

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To link to this item DOI: 10.1080/00397911.2021.1960376

Abstract/Summary

Herein, we report a new method of synthesis of N-acylureas (E1-5) via reaction of dibenzoylhydrazine carboxamide (N,2-bis(4-methoxybenzoyl)hydrazine-1-carboxamide) (C) and various benzylamines. Preparation of dibenzoylhydrazine carboxamide was performed by the treatment of 5,6-diaryl-3-methylthio-1,2,4-triazine (B) with Oxone which leads to oxidation and triazine ring cleavage in high yield (82%). Five benzylamine derivatives containing different electron donating and withdrawing substituents were used in this study. Yields for the conversion of dibenzoylhydrazine carboxamide (C) to N-acylureas (E1-5) were in the range of 40-55%. The structures of the intermediates and final products were characterized and confirmed by NMR, mass spectrometry and single-crystal X-ray crystallography.

Item Type:Article
Refereed:Yes
Divisions:Interdisciplinary centres and themes > Chemical Analysis Facility (CAF)
Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Xray (CAF)
ID Code:100577
Uncontrolled Keywords:N-Benzyl-N’-acylurea, Ureide, Carbamoylbenzamide, X-ray crystallography
Publisher:Taylor and Francis

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