Title compounds were obtained starting from the key imidazole intermediate, 5-​amino-​1-​phenylmethyl-​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-​mercaptohypoxanthines, 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 hypoxanthines 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.

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

GIORGI, IRENE;
2005

Abstract

Title compounds were obtained starting from the key imidazole intermediate, 5-​amino-​1-​phenylmethyl-​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-​mercaptohypoxanthines, 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 hypoxanthines 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.
Biagi, G.; Giorgi, Irene; Livi, O; F., Pacchini; O., Salerni; V., Scartoni
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/203350
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