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A new synthesis of 4-cyano-1,3-dihydro-2-oxo-2H-imidazole-5-(N1-tosy1)carboxamide : reactive precursor for thiopurine analogues

✍ Scribed by Abdel-Sattar S. Hamad; Hamed D. A. Y. Derbala

Publisher
Journal of Heterocyclic Chemistry
Year
2001
Tongue
English
Weight
84 KB
Volume
38
Category
Article
ISSN
0022-152X

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✦ Synopsis

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‐toluenesulfon‐amide 2. The N‐[(Z)‐2‐amino‐1,2‐dicycanovinyl carbamoyl]‐p‐toluenesulfonamide 2 was reacted readily with two molar amount of p‐nitrobenzaldehyde at room temperature in the presence of base to give 7,8‐dihy‐dro‐2‐(4‐nitrophenyl)‐8‐oxo‐9‐tosylpurine‐6‐carboxamide 8. Thiation of compounds 3 and 8 using Lawesson's reagent in tetrahydrofuran gave novel thioimidazoles 4, 5, and 6 and thiopurines 9, 10, and 11, which have been characterized spectroscopically.

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