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Acid and base catalyzed intramolecular cyclizations ofN-benzoylthiocarbamoyl-acetals

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Abstract

Acid and base catalyzed intramolecular cyclizations ofN-benzoylthioureidoacetal, containing four functional groups adjacent to thiourea such as benzocarbamoyl, acetal, thioure and amide, were investigated. The condensation reaction ofN-benzoyl thiocarbamoylglycine amide in the presence of 10% aqueous NaOH provided 1-(2,2-dimethoxy)ethyl-imidazolidine-2-thione exclusively. In the presence of pyridine, it was transformed to 2-thiohydantoin.N-Benzoyl thiocarbamoyl glycine amide was completely transformed to an iminothiazolidine exclusively in the presence of Lewis acid such as borontrifluoride etherate or trimethylsilyl iodide. 1-(2,2-Dimethoxy)ethyl-imidazolidine-2-thione was transformed to imidazole[2,1-b]thiazole and pyrazino[5,1-a]imidazole in the presence of BF3.Et2O and formic acid, respectively.

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Authors and Affiliations

  1. Yuhan Research Center, 27-3 Tangjeong-Dong, 435-715, Kunpo, Kyonggi-Do, Korea

    Bongyong Lee Ph.D. & Jong Wook Lee

  2. Korea Institute of Science & Technology, Cheongryang, P.O. Box 131, 130-650, Seoul, Korea

    Choongsup Kim

Authors
  1. Bongyong Lee Ph.D.
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  2. Choongsup Kim
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  3. Jong Wook Lee
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Correspondence to Bongyong Lee Ph.D..

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Lee, B., Kim, C. & Lee, J.W. Acid and base catalyzed intramolecular cyclizations ofN-benzoylthiocarbamoyl-acetals. Arch Pharm Res 23, 99–103 (2000). https://doi.org/10.1007/BF02975496

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  • DOI: https://doi.org/10.1007/BF02975496

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