Solid phase synthesis of dihydropyrimidinones and pyrimidinone carboxylic acids from malonic acid resin

Authors
Hamper, BC Gan, KZ Owen, TJ
Citation
Bc. Hamper et al., Solid phase synthesis of dihydropyrimidinones and pyrimidinone carboxylic acids from malonic acid resin, TETRAHEDR L, 40(27), 1999, pp. 4973-4976
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
27
Year of publication
1999
Pages
4973 - 4976
Database
ISI
SICI code
0040-4039(19990702)40:27<4973:SPSODA>2.0.ZU;2-J
Abstract
Malonic acid resin 1 and the corresponding diester 2 have been used for the preparation of dihydropyrimidinones 6 and pyrimidinone carboxylic acids 8. Knoevenagel condensation of the unsymmetrical resin bound malonate diester 2 followed by condensation with amidines provides dihydropyrimidinone carb oxylate esters 4. Cleavage of 4 with TFA afforded the caboxylic acid 5 whic h undergoes decarboxylation to give dihydropyrimidinone 6. Oxidation of 4 w ith CAN followed by cleavage with TFA gave pyrimidinone carboxylic acids 8. (C) 1999 Elsevier Science Ltd. All rights reserved.