Microwave-Assisted Synthesis of Substituted Pyrazoles and Pyrazolo [3, 4-d]thiopyrimidines

Ethyl(ethoxymethylene)cyanoacetate and ethoxymethylene malononitrile were synthesized from the reaction of malononitrile or ethylcyanoacetate with triethyl orthoformate or orthoacetate in N, N-dimethylacetamide under microwave irradiation. In a similar manner, substituted pyrazoles were synthesized...

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Published inPhosphorus, sulfur, and silicon and the related elements Vol. 181; no. 3; pp. 591 - 599
Main Authors Heravi, Majid M., Nami, Navabeh, Seifi, Nasim, Oskooie, Hossein A., Hekmatshoar, Rahim
Format Journal Article
LanguageEnglish
Published ABINGDON Taylor & Francis Group 01.03.2006
Taylor & Francis
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Ethylcyanoacetate
malononitrile
Physical Sciences
pyrazolo[3,4-d]thiopyrimidine
Science & Technology
triethyl orthoacetate
triethyl orthoformate
triethyl orthoacetate
triethyl orthoformate
SOLVENT-FREE CONDITIONS
ALKYLATION
ethylcyanoacetate
malononitrile
REGIOSELECTIVE SYNTHESIS
HETEROCYCLIZATION
pyrazolo[3,4-d]thiopyrimidine
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Summary:Ethyl(ethoxymethylene)cyanoacetate and ethoxymethylene malononitrile were synthesized from the reaction of malononitrile or ethylcyanoacetate with triethyl orthoformate or orthoacetate in N, N-dimethylacetamide under microwave irradiation. In a similar manner, substituted pyrazoles were synthesized from the reaction of ethyl (ethoxymethylene)cyanoacetate and ethoxymethylene malononitrile with phenylhydrazine. These pyrazoles were converted to pyrazolo[3, 4-d]thiopyrimidines upon treatment with arylisothiocyanate and thiourea under microwave irradiation.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426500500269646