Cu-catalyzed in situ generation of thiol using xanthate as a thiol surrogate for the one-pot synthesis of benzothiazoles and benzothiophenes.
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.
Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu-600 036, India.
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Prasad
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Sekar
D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry; D014970:Xanthines / Q000737:chemistry*
D052160:Benzothiazoles; D009942:Organometallic Compounds; D013438:Sulfhydryl Compounds; D013876:Thiophenes; D014970:Xanthines; C088015:benzothiophene; D003300:Copper