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Hypervalent Iodine(III) Mediated Synthesis of 3-Substituted 5-Amino-1,2,4-thiadiazoles through Intramolecular Oxidative S-N Bond Formation

Arumugam Mariappan, Kandasamy Rajaguru, Noufal Merukan Chola, Shanmugam Muthusubramanian* and Nattamai Bhuvanesh

*Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, Email:

A. Mariappan, K. Rajaguru, N. M. Chola, S. Muthusubramanian, N. Bhuvanesh, J. Org. Chem., 2016, 81, 6573-6579.

DOI: 10.1021/acs.joc.6b01199

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An intramolecular oxidative S-N bond formation of imidoyl thioureas mediated by phenyliodine(III) bis(trifluoroacetate) enables an efficient, metal-free synthesis of 3-substituted-5-arylamino-1,2,4-thiadiazoles. The protocol offers broad substrate scope, very short reaction times and very good yields.

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Key Words

1,2,4-thiadiazoles, PIFA

ID: J42-Y2016