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SYNTHESIS OF ISOXAZOLE AND AZOLE ENSEMBLES BASED ON 1,3-DIPOLAR CYCLOADDITION REACTION OF ENAMINES WITH NITRILE OXIDES

Илья В. Ефимов, Юрий М. Шафран, Наталья Н. Волкова, Николай А. Беляев, Павел А. Слепухин, Василий А. Бакулев
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Abstract


2-(1,2,3-Thiadiazol-5-yl)enamines and 3-(1,2,3-triazol-4-yl)enaminones react with arylhydroxamoyl chlorides at room temperature with the exclusive formation of 3-aryl-4-(1,2,3-thiadiazol-5-yl)- and [4-(1,2,3-triazol-4-yl)carbonyl]isoxazoles in high yields. The proposed mechanism includes in situ generation of nitrile oxides, which participate in the (3+2)-dipolar cycloaddition reactions leading to the formation of the isoxazole ring.

Authors: Ilya V. Efimov, Yuri M. Shafran, Natalya N. Volkova, Nikolay A. Belyaev, Pavel A. Slepukhin, Vasiliy A. Bakulev*

 


Keywords


enamines; hydroxamoyl chlorides; isoxazoles; cycloaddition; regioselectivity

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