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Issue 10, 2013
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Cu-catalyzed in situ generation of thiol using xanthate as a thiol surrogate for the one-pot synthesis of benzothiazoles and benzothiophenes

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Abstract

A new copper-catalyzed in situ generation of aryl thiolates strategy was successfully developed for the one-pot synthesis of substituted benzothiazoles from 2-iodoanilides using xanthate as a thiol precursor. A wide range of 2-iodoanilides with both electron-releasing and electron-withdrawing groups produced the corresponding benzothiazoles in good yields. Further, this one-pot protocol was successfully utilized for the synthesis of a potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzo[d]thiazole (PMX 610). Finally, the copper-catalyzed in situ generation of aryl thiolates strategy was successfully applied for the domino synthesis of substituted benzothiophenes from o-haloalkynyl benzenes using xanthate as a thiol precursor.

Graphical abstract: Cu-catalyzed in situ generation of thiol using xanthate as a thiol surrogate for the one-pot synthesis of benzothiazoles and benzothiophenes

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Publication details

The article was received on 29 Sep 2012, accepted on 08 Jan 2013 and first published on 08 Jan 2013


Article type: Paper
DOI: 10.1039/C3OB26915A
Org. Biomol. Chem., 2013,11, 1659-1665

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    Cu-catalyzed in situ generation of thiol using xanthate as a thiol surrogate for the one-pot synthesis of benzothiazoles and benzothiophenes

    D. J. C. Prasad and G. Sekar, Org. Biomol. Chem., 2013, 11, 1659
    DOI: 10.1039/C3OB26915A

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