Article
Solid-phase Synthesis of 5,6-dihydropyrimidine-2,4-diones
Tetrahedron Letters
(1996)
Abstract
A series of 1,3-disubstituted-5,6-dihydropyrimidine-2,4-diones 1 are prepared by solid phase organic chemistry using a cyclization-cleavage strategy from readily available amines and isocyanates. An acrylate ester of Wangs resin is treated with primary amines to afford N-substituted β-aminoesters followed by treatment with isocyanates to afford β-ureido ester 4. Cyclization-cleavage of the bound ureido ester under acidic conditions gave direct formation of 5,6-dihydropyrimidinedione 1.
Reaction of polymer bound acylates with amines provides β-amino esters which can be treated with isocyanates and cyclized to give 1,3-disubstituted-5,6-dihydropyrimidine-2,4-diones.
Disciplines
Publication Date
July 1, 1996
DOI
10.1016/0040-4039(96)01103-3
Citation Information
Stephen A. Kolodziej and Bruce C. Hamper. "Solid-phase Synthesis of 5,6-dihydropyrimidine-2,4-diones" Tetrahedron Letters Vol. 37 Iss. 30 (1996) p. 5277 - 5280 Available at: http://works.bepress.com/bruce-hamper/27/