REACTIONS OF 6-AMINOPYRIMIDIN-4(3H)-ONES WITH ELECTRON-DEFICIENT ALKENYL DERIVATIVES - EASY PREPARATION OF HETEROCYCLIC-ANALOGS OF SANGIVAMICINE

Authors
COBO J SANCHEZ A NOGUERAS M
Citation
J. Cobo et al., REACTIONS OF 6-AMINOPYRIMIDIN-4(3H)-ONES WITH ELECTRON-DEFICIENT ALKENYL DERIVATIVES - EASY PREPARATION OF HETEROCYCLIC-ANALOGS OF SANGIVAMICINE, Tetrahedron, 54(21), 1998, pp. 5753-5762
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
21
Year of publication
1998
Pages
5753 - 5762
Database
ISI
SICI code
0040-4020(1998)54:21<5753:RO6WEA>2.0.ZU;2-4
Abstract
The electron-deficient maleic derivatives, maleic anhydride and maleim ide, act against 6-aminopyrimidines almost exclusively as activated al kenyl derivatives, affording Michael adducts which in the case of less reactive maleimide are stable and can be isolated, and in the case of maleic anhydride those adducts evolve to pyrrolo[2,3-d]pyrimidines. D ienophilic character of maleimide towards 6-aminopyrimidin-4(3H)-one c ould also be observed in one case, where a pyrrolo[3,4-c]pyridine deri vative was isolated. (C) 1998 Elsevier Science Ltd. All rights reserve d.