Cyclofunctionalization of 6-alkenylsulfanylpyrazolo[3,4-d]-pyrimidin-4(5H)-ones with arenesulfenyl chlorides View Full Text


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Article Info

DATE

2009-12

AUTHORS

A. I. Vas’kevich, A. V. Bentya, V. I. Staninets

ABSTRACT

Reactions of 6-allylsulfanylpyrazolo[3,4-d]pyrimidin-4(5H)-one with arenesulfenyl chlorides in chloroform gave products of addition of the latter at the exocyclic double bond, while analogous reactions in acetic acid in the presence of LiClO4 were accompanied by intramolecular electrophilic cyclization involving the N7 atom. 6-Cinnamylsulfanylpyrazolo[3,4-d]pyrimidin-4(5H)-one reacted with arenesulfenyl chlorides in acetic acid in the absence of electrolyte to produce fused pyrazolo[4′,3′: 5,6]pyrimido[2,1-b][1,3]thiazine derivatives. Introduction of a bulky phenyl group into position 1 of the pyrazolo[3,4-d]pyrimidine system reduces the yield of the corresponding intramolecular cyclization product at N7 as a result of concurrent formation of acyclic addition product. DOI More... »

PAGES

1847-1852

References to SciGraph publications

  • 2008-09. Electrophilic heterocyclization of 6-alken(yn)ylsulfanyl-pyrazolo[3,4-d]pyrimidin-4(5H)-ones in RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
  • 1995-05. Sulfenocyclization of unsaturated ureas and thioureas in MONATSHEFTE FÜR CHEMIE - CHEMICAL MONTHLY
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    http://scigraph.springernature.com/pub.10.1134/s1070428009120161

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    http://dx.doi.org/10.1134/s1070428009120161

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