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, Nagesh Jatangi, Radha Krishna Palakodety, Sridhar Balasubramanian and Mangarao Nakka*

*Organic and Biomolecular Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India, Email: drmangaraogmail.com

N. Tumula, N. Jatangi, R. K. Palakodety, S. Balasubramanian, M. Nakka, J. Org. Chem., 2017, 82, 5310-5316.

DOI: 10.1021/acs.joc.7b00646

Abstract

A molecular iodine-catalyzed oxidative cyclization of 2-aminopyridine/amidine and isothiocyanate via N-S bond formation enables the synthesis of N-fused and 3,4-disubstituted 5-imino-1,2,4-thiadiazole derivatives at ambient temperature. This transition-metal-free protocol provides a facile and highly efficient regiospecific synthesis of various 1,2,4-thiadiazole derivatives with good to excellent yields using inexpensive I₂ as a catalyst.

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Key Words

fused S-heterocycles, fused N-heterocycles, S-heterocycles, N-heterocycles

ID: J42-Y2017

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, Nagesh Jatangi, Radha Krishna Palakodety, Sridhar Balasubramanian and Mangarao Nakka*

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