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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 3
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Original Articles

A Simple, One-Pot Synthesis of N-Alkyl and N-Aryl Thieno[2,3-d]pyrimidinones from Thiophene- and Benzothiophene-2-yl-ureas

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Pages 337-344 | Received 20 May 2011, Accepted 10 Jun 2011, Published online: 02 Nov 2012
 

Abstract

We herein describe a convenient, one-pot synthesis of N-substituted thieno and benzothieno[2,3-d]pyrimidinones from the respective thiophene-2-yl ureas. This intramolecular cyclization, which presumably proceeds via a Vilsmeier–Haack dimethyliminium intermediate, has proven to be regioselective when performed in the presence of N,N′-bisarylureas and allows for independent functionalization of the pyrimidinone N3 and C4 positions.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

The authors would like to thank Craig Avery for useful discussion, and Biota Europe Ltd (UK) for support during the course of this research.

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