Intramolecular rearrangement of α-amino acid amide derivatives of 2-aminobenzothiazoles |
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Authors: | Jeffrey C Pelletier Venkata VelvadapuMark E McDonnell Jay E WrobelAllen B Reitz |
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Institution: | Fox Chase Chemical Diversity Center, Inc., 3805 Old Easton Rd., Doylestown, PA 18902, United States |
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Abstract: | We have found that α-amino acid amide derivatives of 2-aminobenzothiazoles undergo a time-dependent, thermal rearrangement in which the amine group attacks the 2-position carbon of the thiazole ring to form a 5,5-spiro ring system. This is followed by sulfur leaving and air oxidation to the corresponding symmetrical disulfide. The isolated yields of such products are quite high (>70%) if there is conformational bias to further promote the intramolecular reaction such as for the 2-aminobenzothiazole amides derived from proline or 4-aminopiperidine-4-carboxylic acid. This rearrangement has not been described previously for α-amino acid amide derivatives of 2-aminobenzothiazoles. However, a related reaction involving 2-semicarbazido benzothiazoles has been recently reported. |
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Keywords: | 2-Aminobenzothiazole Rearrangement Riluzole amides Diphenyldisulfide Prodrugs |
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