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Synthesis 2015; 47(09): 1227-1237
DOI: 10.1055/s-0034-1380321
DOI: 10.1055/s-0034-1380321
feature
Straightforward Synthesis of Functionalized Furo[3,4-d]pyrimidine-2,4-diones
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
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380321.
- Supporting Information
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