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; Nattamai Bhuvanesh

doi:10.1021/acs.joc.6b01199

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

J Org Chem. 2016 Aug 5;81(15):6573-9. doi: 10.1021/acs.joc.6b01199. Epub 2016 Jul 19.

Authors

Arumugam Mariappan¹, Kandasamy Rajaguru¹, Noufal Merukan Chola¹, Shanmugam Muthusubramanian¹, Nattamai Bhuvanesh²

Affiliations

¹ Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University , Madurai 625 021, India.
² X-ray Diffraction Laboratory, Department of Chemistry, Texas A&M University , College Station, Texas 77842, United States.

PMID: 27379380
DOI: 10.1021/acs.joc.6b01199

Abstract

An efficient synthesis of 3-substituted-5-arylamino-1,2,4-thiadiazoles through intramolecular oxidative S-N bond formation of imidoyl thioureas by phenyliodine(III) bis(trifluoroacetate) is reported. The protocol features a metal-free approach, broad substrate scope, very short reaction times, good to excellent yields, and simple starting materials.

Publication types

Research Support, Non-U.S. Gov't