A new synthesis of 4-Cyano-1,3-dihydro-2-oxe-2H-imidazole-5(N-1-tosyl)carboxamide: Reactive precursor for thiopurine analogues

Citation
Ass. Hamad et Hay. Derbala, A new synthesis of 4-Cyano-1,3-dihydro-2-oxe-2H-imidazole-5(N-1-tosyl)carboxamide: Reactive precursor for thiopurine analogues, J HETERO CH, 38(4), 2001, pp. 939-944
Citations number
21
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022-152X → ACNP
Volume
38
Issue
4
Year of publication
2001
Pages
939 - 944
Database
ISI
SICI code
0022-152X(200107/08)38:4<939:ANSO4>2.0.ZU;2-0
Abstract
N-[(5-Cyano-2-oxoimidazolidin-4-yl)-iminomethyl]-p-toluensulfonamide 3 was prepared in fairly good yield by the base catalyzed cyclisation of N-[(Z)-2 -amino-1,2-dicycanovinylcarbamoyl]-p-toluenesulfonamide 2. The N-[(Z)-2-ami no-1,2-dicycanovinyl carbamoyl]-p-toluenesulfonamide 2 was reacted readily with two molar amount of p-nitrobenzaldehyde at room temperature in the pre sence of base to give 7,8-dihydro-2-(4-nitrophenyl)-8-oxo-9-tosylpurine-6-c arboxamide 8. Thiation of compounds 3 and 8 using Lawesson's reagent in tet rahydrofuran gave novel thioimidazoles 4, 5, and 6 and thiopurines 9, 10, a nd 11, which have been characterized spectroscopically.