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Synfacts 2011(8): 0827-0827  
DOI: 10.1055/s-0030-1260847
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Cu-Mediated Heteroannulation Route to 2-Thio-Substituted Benzothiazoles

Contributor(s): Victor Snieckus, Toni Rantanen
L. Shi, X. Liu, H. Zhang, Y. Jiang, D. Ma*
Shanghai University and Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

Reported is a condensation of carbon disulfide with thiols to generate carbonotri­thioate salts in situ, which upon copper-mediated coupling with 2-iodoanilines and intramolecular cyclization affords 2-thiobenzothiazoles in a one-pot procedure in moderate to good yields. Several copper sources were screened but, in all cases, it was shown that three equivalents are necessary to obtain reasonable yields of products. Changing the solvent proved to be detrimental. The substrate scope was well studied in terms of functional group compatibility but no substrates bearing ortho substituents to the iodine or the NH2 were tested.