Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

I2-Catalyzed Oxidative N–S Bond Formation: Metal-Free Regiospecific Synthesis of N-Fused and 3,4-Disubstituted 5-Imino-1,2,4-thiadiazoles

I2-Catalyzed Oxidative N–S Bond Formation: Metal-Free Regiospecific Synthesis of N-Fused and 3,4-Disubstituted 5-Imino-1,2,4-thiadiazoles
Nagaraju Tumula, Radha Krishna Palakodety, Nagesh Jatangi, Mangarao Nakka, Sridhar Balasubramanian
A novel and expeditious approach for the synthesis of N-fused and 3,4-disubstituted 5-imino-1,2,4-thiadiazole derivatives has been achieved through the molecular iodine-catalyzed oxidative cyclization of 2-aminopyridine/amidine and isothiocyanate via N–S bond formation at ambient temperature. The present one-pot transition-metal-free protocol provides the facile and highly efficient regiospecific synthesis of various 1,2,4-thiadiazole derivatives in a scaled-up manner with good to excellent yields using inexpensive I2 as a catalyst.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00646

DOI: 10.1021/acs.joc.7b00646

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