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I2-Mediated Oxidative C-N and N-S Bond Formation in Water: A Metal-Free Synthesis of 4,5-Disubstituted/N-Fused 3-Amino-1,2,4-triazoles and 3-Substituted 5-Amino-1,2,4-thiadiazoles

Nagesh Jatangi, Nagaraju Tumula, Radha Krishna Palakodety and Mangarao Nakka*

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

N. Jatangi, N. Tumula, R. K. Palakodety, M. Nakka, J. Org. Chem., 2018, 83, 5715-5723.

DOI: 10.1021/acs.joc.8b00753 (free Supporting Information)


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Abstract

I2-mediated oxidative C-N and N-S bond formations in water enable a metal-free, environmentally benign and convenient strategy for the synthesis of 4,5-disubstituted/N-fused 3-amino-1,2,4-triazoles and 3-substituted 5-amino-1,2,4-thiadiazoles from isothiocyanates. The scalable protocols exhibited excellent substrate tolerance.

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Key Words

1,2,4-triazoles, 1,2,4-thiadiazoles, 1,2,4-triazolo[4,3-a]pyridines, green chemistry, iodine


ID: J42-Y2018