4.5 Article

DABCO-Promoted Bicyclization/Rearrangement Reaction Synthesis of Tetrasubstituted Furans and Furo[3,4-d]pyrimidine-2,4-diones from 1,4-Enediones

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume -, Issue -, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202300810

Keywords

1,4-Enediones; Cyanamide; Polysubstituted furans; Bicyclization; Synthesis

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A DABCO-promoted bicyclization/rearrangement reaction has been developed for the synthesis of tetrasubstituted furans from 1,4-enediones at room temperature. This transformation involves aza-Michael addition, intramolecular bicyclization, and rearrangement processes. In addition, the 4-ureidofuran-3-carboxylate ester products can further be converted to furo[3,4-d]pyrimidine-2,4-diones through intramolecular substitution cyclization under heating conditions.
A DABCO-promoted bicyclization/rearrangement reaction has been developed for the synthesis of tetrasubstituted furans from 1,4-enediones at room temperature. This transformation involves aza-Michael addition, intramolecular bicyclization, and rearrangement processes. In addition, the 4-ureidofuran-3-carboxylate ester products can further be converted to furo[3,4-d]pyrimidine-2,4-diones through intramolecular substitution cyclization under heating conditions.

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