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Synthesis of new 1,1′-carbonyl-bis[3-aryl(heteroaryl)-5-(trihalomethyl)-1H-pyrazoles] and trifluoromethyl derivatives through ring-opening reactions

✍ Scribed by Helio G. Bonacorso; Cleber A. Cechinel; Liliane M. F. Porte; Jussara Navarini; Susiane Cavinatto; Ronan C. Sehnem; Demetrius B. Martins; Nilo Zanatta; Marcos A. P. Martins

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
132 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis

Two new series of 1,1 0 -carbonyl-bis[3-aryl(heteroaryl)-5-trihalomethyl-1H-pyrazoles], where aryl ¼ 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 0 -BiPh, 1-naphthyl, and heteroaryl ¼ 2thienyl and 2-furyl have been synthesized, in a one-pot methodology, from the reaction of 4-methoxy-4aryl(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.

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Oxidative ring-opening of rel-(2R,3R,5S)
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## Abstract __rel__‐(2__R__,3__R__)‐__N__‐Benzoylamino‐6,7‐bis(methoxycarbonyl)‐2,3‐dihydro‐1‐oxo‐1__H__,5__H__‐pyrazolot[1,2‐__a__]‐pyrazoles 5, accesible by cycloaddition of dimethyl acetylenedicarboxylate (3) to (1Z)‐__rel__‐(4__R__,5__R__)‐1‐aryl‐methylidene‐4‐benzoylamino‐5‐phenyl‐3‐pyrazolidi