ACID-CATALYZED REACTIONS OF 5-FORMYLURACILS WITH ENAMINES - A FACILE SYNTHESIS OF 5-ACYLVINYLURACILS

Authors
SINGH H",DOLLY,"HUNDAL MS HUNDAL G SINGH P CHIMNI SS KUMAR S
Citation
Ms. Singh H",dolly,"hundal et al., ACID-CATALYZED REACTIONS OF 5-FORMYLURACILS WITH ENAMINES - A FACILE SYNTHESIS OF 5-ACYLVINYLURACILS, Tetrahedron, 54(26), 1998, pp. 7563-7572
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
26
Year of publication
1998
Pages
7563 - 7572
Database
ISI
SICI code
0040-4020(1998)54:26<7563:ARO5WE>2.0.ZU;2-N
Abstract
5-Formyl-1,3-dimethyluracil (1) reacts with secondary amine derived en amines of ketones and aldehydes to provide 5-(acyvinyl)uracil derivati ves. The presence of a CH3 group at C-6 of 1 induces a competitive ann ulation reaction. Depending on the bulk of substituents 5-(acylvinyl)u racils acquire cis -diene and E or Z configurations on the vinyl unit. Enamines derived from 1,3-cyclohexanedione and ethyl acetoacetate rea ct with 1 in 1: 2 stoichiometric manner to provide 5-(9-xanthenyl)urac il and 5-(6-cycohexadienyl)uracil(X-ray) derivatives. (C) 1998 Elsevie r Science Ltd. All rights reserved.