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Intramolecular Rearrangement of α-Amino Acid Amide Derivatives of 2-Aminobenzothiazoles

Intramolecular Rearrangement of α-Amino Acid Amide Derivatives of 2-Aminobenzothiazoles

Jeffrey C Pelletier, Venkata Velvadapu, Mark E McDonnell, Jay E Wrobel, Allen B Reitz

Tetrahedron Lett. 2014 Jul 23;55(30):4193-4195.

PMID: 25018567

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP499193543	3-Trimethylsilanylethynyl-pyridine-2-carboxylic acid amide		499193-54-3	Price

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