Chemoselectivity in the Oxidation of unsymmetrical Thioureas with NBS/sulfuric Acid: Benzothiazoles vs. 1,2,4-Thiadiazoles

J. Ganín Departamento de Química Orgánica, Facultad de Ciencias, ICMA, Universidad de Zaragoza-CSIC, E-50009, Zaragoza, Spain

E. Meléndez Departamento de Química Orgánica, Facultad de Ciencias, ICMA, Universidad de Zaragoza-CSIC, E-50009, Zaragoza, Spain

F. L. Merchán Departamento de Química Orgánica, Facultad de Ciencias, ICMA, Universidad de Zaragoza-CSIC, E-50009, Zaragoza, Spain

P. Merino Departamento de Química Orgánica, Facultad de Ciencias, ICMA, Universidad de Zaragoza-CSIC, E-50009, Zaragoza, Spain

J. Orduna Departamento de Química Orgánica, Facultad de Ciencias, ICMA, Universidad de Zaragoza-CSIC, E-50009, Zaragoza, Spain

T. Tejero Departamento de Química Orgánica, Facultad de Ciencias, ICMA, Universidad de Zaragoza-CSIC, E-50009, Zaragoza, Spain

Abstract

Exclusive formation of 2-heteroarylaminobenzothiazoles is observed when N-aryl-N′-heteroarylthioureas are treated with NBS/H₂SO₄. A possible explanation to account for the lack of 1,2,4-thiadiazole formation is offered, and a previous report³ concerning the oxidation of N-phenyl-N′-(2-pyridyl)thiourea is shown to be erroneous.

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Chemoselectivity in the Oxidation of unsymmetrical Thioureas with NBS/sulfuric Acid: Benzothiazoles vs. 1,2,4-Thiadiazoles

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Chemoselectivity in the Oxidation of unsymmetrical Thioureas with NBS/sulfuric Acid: Benzothiazoles vs. 1,2,4-Thiadiazoles

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