Synthesis 2015; 47(09): 1227-1237
DOI: 10.1055/s-0034-1380321
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© Georg Thieme Verlag Stuttgart · New York

Straightforward Synthesis of Functionalized Furo[3,4-d]pyrimidine-2,4-diones

Laurens M. De Coen
Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent 9000, Belgium   Email: Chris.Stevens@UGent.be
,
Martyna Jatczak
Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent 9000, Belgium   Email: Chris.Stevens@UGent.be
,
Koen Muylaert
Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent 9000, Belgium   Email: Chris.Stevens@UGent.be
,
Sven Mangelinckx
Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent 9000, Belgium   Email: Chris.Stevens@UGent.be
,
Christian V. Stevens*
Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, Ghent 9000, Belgium   Email: Chris.Stevens@UGent.be
› Author Affiliations
Further Information

Publication History

Received: 15 January 2015

Accepted after revision: 18 February 2015

Publication Date:
19 March 2015 (online)

Abstract

An efficient synthesis of furo[3,4-d]pyrimidine-2,4-diones has been accomplished via a straightforward three-step pathway. Curtius rearrangement of 4-(methoxycarbonyl)furan-3-carboxylic acid and subsequent reaction with a variety of amines resulted in the corresponding intermediate ureids, which could be ring closed to the bicyclic scaffold in good yields. Functionalization of N-1 afforded a small library of new heterocycles. (Partial) hydrogenation of the furo[3,4-d]pyrimidine-2,4-diones led to the 5,7-dihydro- and tetrahydrofuro[3,4-d]pyrimidine-2,4-diones.

Supporting Information

 
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