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Convenient One-Pot Two-Step Synthesis of Symmetrical and Unsymmetrical Diacyl Ureas, Acyl Urea/Carbamate/Thiocarbamate Derivatives, and Related Compounds

Anolan Garcia Hernandez, Gregory M. Grooms, Abir T. El-Alfy, Jozef Stec*

*Chicago State University, College of Pharmacy, Department of Pharmaceutical Sciences, 9501 S. King Drive, Chicago, IL 60628, USA, Email: jstecketchum.edu

A. G. Hernandez, G. M. Grooms, A. T. El-Alfy, J. Stec, Synthesis, 2017, 49, 2163-2176.

DOI: 10.1055/s-0036-1588724 (free Supporting Information)


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Abstract

Acyl isocyanates generated by the reaction of primary amides with oxalyl chloride react with a wide range of amides, hydrazides, amines, alcohols, carbazate, and sulfonate to provide symmetrical and unsymmetrical diacyl urea derivatives, acyl ureas/carbamates/thiocarbamates, and related compounds. This convenient one-pot, two-step synthesis uses cheap and commercially available starting reagents.


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Key Words

bioisostere, urea derivaties, acyl isocyanates, symmetrical/unsymmetrical diacyl ureas, acyl ureas, acyl carbamates, carbamates, acyl thiocarbamates


ID: J66-Y2017