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Microwave-assisted synthesis of 5-trichloromethyl substituted 1-phenyl-1H-pyrazoles and 1,2-dimethylpyrazolium chlorides

✍ Scribed by Marcos A.P Martins; Claudio M.P Pereira; Paulo Beck; Pablo Machado; Sidnei Moura; Marcos V.M Teixeira; Helio G Bonacorso; Nilo Zanatta

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
141 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

A series of five 5-trichloromethyl-1-phenyl-1H-pyrazoles and six 5-trichloromethyl-1,2-dimethylpyrazolium chlorides have been synthesized in 80-98% yield by environmentally benign microwave induced techniques involving the cyclocondensation of 4-alkoxy-1,1,1-trichloro-3-alken-2-ones [Cl 3 C(O)C(R 2 )=C(R 1 )OR, where R 2 =H, Me; R 1 =H, alkyl, phenyl and R=Me, Et] with phenyl hydrazine and 1,2-dimethylhydrazine dihydrochloride, respectively, using toluene as solvent. The use of microwave and classical methods are comparable for making pyrazoles, but the formation of pyrazolium chlorides can be achieved in a significant shorter time, and in some cases better yield.

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