Electrophilic heterocyclization of 6-alken(yn)ylsulfanyl-pyrazolo[3,4-d]pyrimidin-4(5H)-ones

6-Allylsulfanyl-1-arylpyrazolo[3,4- d ]pyrimidin-4(5 H )-ones react with iodine and sulfuric acid to give angular pyrazolothiazolopyrimidine derivatives. The reaction of 6-(prop-2-yn-1-ylsulfanyl)-1-(4-tolyl)-pyrazolo[3,4- d ]pyrimidin-4(5 H )-one with sulfuric acid gives angularly fused pyrazolo[4,...

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Bibliographic Details
Published in:Russian journal of organic chemistry 2008-09, Vol.44 (9), p.1362-1368
Main Authors: Bentya, A. V., Vas’kevich, R. I., Bol’but, A. V., Vovk, M. V., Staninets, V. I., Turov, A. V., Rusanov, E. B.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Iodine
Organic Chemistry
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Summary:6-Allylsulfanyl-1-arylpyrazolo[3,4- d ]pyrimidin-4(5 H )-ones react with iodine and sulfuric acid to give angular pyrazolothiazolopyrimidine derivatives. The reaction of 6-(prop-2-yn-1-ylsulfanyl)-1-(4-tolyl)-pyrazolo[3,4- d ]pyrimidin-4(5 H )-one with sulfuric acid gives angularly fused pyrazolo[4,3- e ][1,3]thiazolo-[3,2- a ]pyrimidin-4-one, whereas in the reaction with sodium methoxide linearly fused pyrazolo[3,4- d ][1,3]-thiazolo[3,2- a ]pyrimidin-4-one was formed. Linearly fused pyrazolo[3′,4′:4,5]pyrimido[2,1- b ][1,3]thiazole derivatives were also obtained by reaction of 1-aryl-6-(3-phenylprop-2-en-1-ylsulfanyl)pyrazolo[3,4- d ]pyrimidin-4(5 H )-ones with sulfuric acid.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428008090194