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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,
Published in Royal Society of Chemistry
2013
PMID: 23358646
Volume: 11
   
Issue: 10
Pages: 1659 - 1665
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. © 2013 The Royal Society of Chemistry.
About the journal
JournalData powered by TypesetOrganic and Biomolecular Chemistry
PublisherData powered by TypesetRoyal Society of Chemistry
ISSN14770520
Open AccessNo
Concepts (12)
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    Benzene
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    Copper
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    Thiophene
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    2-IODOANILIDES
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    ANTI-TUMOR AGENTS
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    Benzothiazoles
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    Electron withdrawing group
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    One-pot protocol
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    One-pot synthesis
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    SITU GENERATION
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    THIOLATES
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    Catalysis