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A new synthesis of 4‐cyano‐1,3‐dihydro‐2‐oxo‐2 H ‐imidazole‐5‐(N 1 ‐tosy1)carboxamide : reactive precursor for thiopurine analogues
Author(s) -
Hamad AbdelSattar S.,
Derbala Hamed D. A. Y.
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380420
Subject(s) - chemistry , reagent , imidazole , yield (engineering) , carboxamide , tetrahydrofuran , base (topology) , amide , medicinal chemistry , nitrile , stereochemistry , organic chemistry , mathematical analysis , materials science , mathematics , solvent , metallurgy
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.