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 |
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Authors: | R I Vas’kevich A I Vas’kevich E B Rusanov V I Staninets M V Vovk |
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Institution: | 1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, Kiev, 02660, Ukraine
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Abstract: | Intramolecular electrophilic cyclization of 6-allylsulfanylpurine by the action of iodine and arenesulfenyl chlorides gave 7-iodomethyl-7,8-dihydro1,3]thiazolo2,3-i]purin-6-ium pentaiodide and 7-arylsulfanylmethyl-7,8-dihydro1,3]thiazolo2,3-i]purin-6-ium perchlorates, respectively. 7-Iodomethyl-7,8-dihydro-1,3]thiazolo2,3-i]purin-6-ium iodide reacted with sodium and potassium alkoxides to produce alkyl N-5-(4-methyl-1,3-thiazol-2-yl)-1H-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]-1H-imidazol-4-amines. Successive treatment of 7-arylsulfanylmethyl-7,8-dihydro1,3]thiazolo2,3-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)-1H-imidazol-4-amines. |
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