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Synthesis of new 1,1′‐carbonyl‐bis[3‐aryl(heteroaryl)‐5‐(trihalomethyl)‐1 H ‐pyrazoles] and trifluoromethyl derivatives through ring‐opening reactions
Author(s) -
Bonacorso Helio G.,
Cechinel Cleber A.,
Porte Liliane M. F.,
Navarini Jussara,
Cavinatto Susiane,
Sehnem Ronan C.,
Martins Demetrius B.,
Zanatta Nilo,
Martins Marcos A. P.
Publication year - 2010
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.427
Subject(s) - chemistry , aryl , trifluoromethyl , ring (chemistry) , medicinal chemistry , derivative (finance) , organic chemistry , alkyl , financial economics , economics
Two new series of 1,1′‐carbonyl‐bis[3‐aryl(heteroaryl)‐5‐trihalomethyl‐1 H ‐pyrazoles], where aryl = C 6 H 5 , 4‐CH 3 C 6 H 4 , 4‐FC 6 H 4 , 4‐OCH 3 C 6 H 4 , 4‐NO 2 C 6 H 4 , 4,4′‐BiPh, 1‐naphthyl, and heteroaryl = 2‐thienyl and 2‐furyl have been synthesized, in a one‐pot methodology, from the reaction of 4‐methoxy‐4‐aryl(heteroaryl)‐1,1,1‐trihalobut‐3‐en‐2‐ones with 1,3‐diaminoguanidine monohydrochloride. The heterocycles were obtained regioselectively in good yields (62–86%) and in a short reaction time. Ring‐opening reactions with 1,2‐dinuleophiles and the synthesis of ethyl carboxylate derivative from a pyrazolycarbohydrazide is also reported. J. Heterocyclic Chem., (2010).