Straightforward Synthesis of Functionalized Furo[3,4-d] pyrimidine-2,4-diones
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 cou...
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Published in | Synthesis (Stuttgart) Vol. 47; no. 9; pp. 1227 - 1237 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
STUTTGART
Thieme Medical Publishers
19.03.2015
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Subjects | |
Online Access | Get more information |
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Summary: | 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. |
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ISSN: | 0039-7881 1437-210X |
DOI: | 10.1055/s-0034-1380321 |