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An efficient, one-pot approach has been described for the synthesis of 3,5-disubstituted isoxazoles from substituted aldoximes (mixture of E and Z) and alkynes, using alkyl nitrites under conventional heating conditions. The key nitrile oxide intermediates that are required for the synthesis of isoxazoles are formed by treatment of substituted aldoxime with either tert-butyl nitrite or isoamyl nitrite. The generated nitrile oxides underwent in situ [3+2] dipolar cycloaddition to the substituted alkynes to give 3,5-disubstituted isoxazoles regioselectively in high to excellent yields. The developed synthetic methodology was applied for the synthesis of a previously reported potent hDGAT1 inhibitor.

A Facile One-Pot Synthesis of 3,5-Disubstituted Isoxazole Derivatives Using Hydroxy (Tosyloxy) Iodobenzene. -The reaction of aromatic aldoximes with aliphatic and aromatic alkynes in the presence of a hypervalent iodine reagent proceeds via an in situ generated reactive nitrile oxide intermediate to provide a direct access to disubstituted isoxazoles. The use of the iodine reagent is of limited utility for synthesizing isoxazoles possessing electron-donating substituents on the aromatic nucleus. The advantage of this protocol is the ease of work-up and easy isolation without any need for column chromatographic purification. -(JADHAV, R. D.; MISTRY HITESH D.; MOTIWALA, H.; KADAM, K. S.; KANDRE, S.; GUPTE*, A.; GANGOPADHYAY, A. K.; SHARMA, R.; J. Heterocycl. Chem. 50 (2013) 4, 774-780, http://dx.

In this study, a novel series of 5‐piperazinethiazole 2,2‐dimethylbutanoic acid and 5‐piperidinethiazole 2,2‐dimethylbutanoic acid derivatives have been synthesized. Structures of the newly synthesized compounds have been elucidated using 1H‐NMR, 13C‐NMR, high‐resolution mass spectroscopy, and high‐performance liquid chromatographic analysis. The synthesized derivatives have been evaluated in vitro for their ability to inhibit the enzyme diacylglycerol acyltransferase 1 responsible for triglyceride biosynthesis.