Issue 1, 2012

A simple direct phosgeneless route to N-heteroaryl unsymmetrical ureas

Abstract

A new simple approach to the synthesis of unsymmetrical ureas HetNC(O)NRR′ (HetNH = pyrrole, indole, carbazole; R, R′ = H, alkyl, aryl) has been explored, which involves the direct reaction of the N-phenoxycarbonyl derivatives of pyrrole, indole and carbazole, HetNCO2Ph, with amines. The aminolysis reaction can be catalyzed by the amidine base DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) under usually very mild conditions and provides a straightforward convenient entry into the target products through a route which avoids the traditional protocols based on multistep procedures and toxic phosgene or phosgene-derivatives.

Graphical abstract: A simple direct phosgeneless route to N-heteroaryl unsymmetrical ureas

Article information

Article type
Paper
Submitted
09 Aug 2011
Accepted
11 Oct 2011
First published
23 Nov 2011

Green Chem., 2012,14, 217-225

A simple direct phosgeneless route to N-heteroaryl unsymmetrical ureas

M. Carafa, V. Mele and E. Quaranta, Green Chem., 2012, 14, 217 DOI: 10.1039/C1GC15984D

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