Synthesis of new imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-one derivatives by iodocyclization of 6-alkenyl(alkynyl)-aminopyrazolo[3,4-d]pyrimidin-4(5H)-ones

6-Allyl(diallyl, prop-2-yn-1-yl)amino-1-R-pyrazolo[3,4- d ]pyrimidin-4(5 H )-ones reacted with iodine to give angularly fused 8-iodomethyl-7,8-dihydro-1-R-imidazo[1,2- a ]pyrazolo[4,3- e ]pyrimidin-4(6 H )-ones which were treated with sodium acetate to obtain 8-methylidene-1-R-7,8-dihydroimidazo[1,2...

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Veröffentlicht in:Russian journal of organic chemistry 2011-07, Vol.47 (7), p.1066-1073
Hauptverfasser: Bentya, A. V., Vas’kevich, R. I., Turov, A. V., Rusanov, E. B., Vovk, M. V., Staninets, V. I.
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Sprache:eng
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Zusammenfassung:6-Allyl(diallyl, prop-2-yn-1-yl)amino-1-R-pyrazolo[3,4- d ]pyrimidin-4(5 H )-ones reacted with iodine to give angularly fused 8-iodomethyl-7,8-dihydro-1-R-imidazo[1,2- a ]pyrazolo[4,3- e ]pyrimidin-4(6 H )-ones which were treated with sodium acetate to obtain 8-methylidene-1-R-7,8-dihydroimidazo[1,2- a ]pyrazolo-[4,3- e ]pyrimidin-4(6 H )-ones as a result of elimination of hydrogen iodide. 8-Methylidene-1-R-7,8-dihydroimidazo[1,2- a ]pyrazolo[4,3- e ]pyrimidin-4(6 H )-ones were converted into 8-methyl-1-R-imidazo[1,2- a ]pyrazolo-[4,3- e ]pyrimidin-4(5 H )-ones on heating to the melting point. 8-Methylidene-1-phenyl-7,8-dihydroimidazo-[1,2- a ]pyrazolo[4,3- e ]pyrimidin-4(6 H )-one underwent isomerization into linearly fused 6-methyl-1-phenyl-1,8-dihydro-4 H -imidazo[1,2- a ]pyrazolo[3,4- d ]pyrimidin-4-one on heating in sulfuric acid.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428011070165