Synthesis of 7-iodo(arylsulfanyl)methyl-7,8-dihydro-[1,3]thiazolo[2,3-i]purinium pentaiodide (perchlorates) and their transformation into 4-amino-5-(1,3-thiazol-2-yl)imidazole derivatives

Intramolecular electrophilic cyclization of 6-allylsulfanylpurine by the action of iodine and arenesulfenyl chlorides gave 7-iodomethyl-7,8-dihydro[1,3]thiazolo[2,3- i ]purin-6-ium pentaiodide and 7-arylsulfanylmethyl-7,8-dihydro[1,3]thiazolo[2,3- i ]purin-6-ium perchlorates, respectively. 7-Iodomet...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2013, Vol.49 (1), p.123-129
Main Authors: Vas’kevich, R. I., Vas’kevich, A. I., Rusanov, E. B., Staninets, V. I., Vovk, M. V.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
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Summary:Intramolecular electrophilic cyclization of 6-allylsulfanylpurine by the action of iodine and arenesulfenyl chlorides gave 7-iodomethyl-7,8-dihydro[1,3]thiazolo[2,3- i ]purin-6-ium pentaiodide and 7-arylsulfanylmethyl-7,8-dihydro[1,3]thiazolo[2,3- i ]purin-6-ium perchlorates, respectively. 7-Iodomethyl-7,8-dihydro-[1,3]thiazolo[2,3- i ]purin-6-ium iodide reacted with sodium and potassium alkoxides to produce alkyl N -[5-(4-methyl-1,3-thiazol-2-yl)-1 H -imidazol-4-yl]formimidates, and its reaction with secondary cyclic amines afforded 5-(4-methyl-1,3-thiazol-2-yl)- N -[morpholin-4-yl(or piperidin-1-yl)methylidene]-1 H -imidazol-4-amines. Successive treatment of 7-arylsulfanylmethyl-7,8-dihydro[1,3]thiazolo[2,3- i ]purin-6-ium perchlorates with sodium acetate and morpholine led to the formation of 5-(4-arylsulfanylmethyl-4,5-dihydro-1,3-thiazol-2-yl)- N -(morpholin-4-ylmethylidene)-1 H -imidazol-4-amines.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428013010211