New C(2)-substituted 8-alkylsulfanyl-9-phenylmethyl-hypoxanthines III

Title compounds were obtained starting from the key imidazole intermediate, 5‐amino‐1‐phenyl‐methyl‐2‐mercapto‐1H‐imidazole‐4‐carboxylic acid amide 5, readily derived from the base catalyzed rearrangement of a thiazole, 5‐amino‐2‐phenylmethylaminothiazole‐4‐carboxylic acid amide 4. Alkylation of the...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2005-07, Vol.42 (5), p.743-749
Main Authors: Biagi, Giuliana, Giorgi, Irene, Livi, Oreste, Pacchini, Federica, Scartoni, Valerio, Salerni, Oreste Leroy
Format: Article
Language:English
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Summary:Title compounds were obtained starting from the key imidazole intermediate, 5‐amino‐1‐phenyl‐methyl‐2‐mercapto‐1H‐imidazole‐4‐carboxylic acid amide 5, readily derived from the base catalyzed rearrangement of a thiazole, 5‐amino‐2‐phenylmethylaminothiazole‐4‐carboxylic acid amide 4. Alkylation of the thiol function on 5 with phenylmethyl and allylic chlorides gave compounds 6 and 7 respectively. Cyclization of 6 with a variety of esters afforded 8‐phenylmethylthiohypoxanthines, 8–11. Similarly, 7 was cyclized to 8‐allylthiohypoxanthines, 20–21. Compound 5 was also cyclized, but formed 8‐mercaptohypox‐anthines, 22–24. Alkylation of 8‐mercaptohypoxanthines afforded 8‐alkylthiohypoxanthines, 8, 9,25 and 26 (see Scheme 2). Chlorination of 9–11 afforded 16–18; adenine 19 was derived from 16. Oxidation of hypox‐anthines 8–11 with m‐chloroperbenzoic acid gave the corresponding 8‐phenylmethylsulfonyl derivatives 12‐15. These derivatives proved resistant to nucleophilic displacement reactions with primary amines.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570420501