The reaction between aryl or heteroarylhydrazines with fluorinated β-diketones (CF3COCH2COR) yields a variety of 3-, 5-, and 3,5-trifluoromethylpyrazoles and 5-trifluoromethyl-5-hydroxy-Δ2-pyrazolines. Twenty-one of such compounds have been isolated and identified by 13C and 19F NMR. Together with the results from the literature they provide a comprehensive overview of the reaction. Semi-empirical calculations at the PM3 level have been used to rationalize these results. The outcome that emerges seems to be that the dehydration of a pair of 3,5-dihydroxypyrazolidines kinetically controls the isomer formed.Key words: hydrazines, 1,3-diketones, pyrazolines, pyrazoles, PM3 calculations.
SummaryThe biological and medicinal properties of 5-aminopyrazoles have prompted enormous research aimed at developing synthetic routes to these heterocyles. This review focuses on the biological properties associated with this system. Various synthetic methods developed up to 2010 for these compounds are described, particularly those that involve the reactions of β-ketonitriles, malononitrile, alkylidenemalononitriles and their derivatives with hydrazines, as well as some novel miscellaneous methods.
Helminthosporium leaf blight (HLB) is the most important disease constraint to wheat (Triticum aestivum L.) cultivation in the eastern Gangetic Plains of South Asia. A Helminthosporium Monitoring Nursery (HMN) including potential adapted and exotic sources of HLB resistance was developed in Bangladesh, India and Nepal to assess the stability of genetic resistance across locations. The 8th, 9th and 10th HMN assessed the HLB resistance and agronomic traits of 17 wheat genotypes across 20 environments of Bangladesh, India and Nepal in the
We report the results obtained when five aromatic or heteroaromatic hydrazines react with sixdiketones bearing trifluoromethyl and aryl substituents. Forty-two compounds have been isolated corresponding to two isomeric trifluoromethyl pyrazoles and the intermediate 5-CF 3 , 5-OH pyrazolines. The results have provided useful information for establishing the mechanism of the synthesis of pyrazoles.
Multinuclear magnetic resonance spectroscopy together with GIAO-DFT calculations allowed establishment of the structure of the products obtained by condensation of 3(5)-amino-4-phenyl-1H-pyrazole and beta-dicarbonyl compounds bearing a trifluoromethyl group. They are 3-phenyl-5-(R)-7-trifluoromethylpyrazolo[1,5-a]pyrimidines.
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