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

Laurens M. De Coen; Martyna Jatczak; Koen Muylaert; Sven Mangelinckx; Christian V. Stevens

doi:10.1055/s-0034-1380321

Synthesis, Table of Contents

Synthesis 2015; 47(09): 1227-1237
DOI: 10.1055/s-0034-1380321

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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

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Abstract

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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.

Key words

heterocycles - ring closure - alkylation - rearrangement - hydrogenation

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References

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