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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Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 47; no. 9; pp. 1227 - 1237
Main Authors De Coen, Laurens M., Jatczak, Martyna, Muylaert, Koen, Mangelinckx, Sven, Stevens, Christian V.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 19.03.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
heterocycles
ring closure
alkylation
MTOR INHIBITORS
hydrogenation
rearrangement
CANCER-THERAPY
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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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0034-1380321