TARGETED ACYLATION AND ARYLSULFONYLATION OF 2-AMINO-6-METHOXY-1,3-BENZOTHIAZOLE
Abstract
Benzothiazoles are important heterocyclic compounds in modern organic synthesis and pharmaceutical chemistry. Numerous biologically active compounds based on the benzothiazole scaffold have been developed, exhibiting anticancer, antimicrobial, anti-inflammatory, antitubercular, antimalarial, anthelmintic, antioxidant, and bactericidal activities [1]. In the present study, targeted acylation and arylsulfonylation of 2-amino-6-methoxy-1,3-benzothiazole (1) with substituted aromatic acid chlorides and arylsulfonyl chlorides were investigated. When the reactions were carried out in benzene solution for 2 hours, with the initial compounds taken in the ratio of 1:acid chlorides:TEA = 1:1.2:1, as well as- 1: arylsulfonyl chlorides:TEA = 1:1:1, amides (2-5, 85-96%) and sulfonamides (6-9, 78-96%) were synthesized in good and high yields. The structure of the synthesized compound was confirmed by the data of IR-, 1H NMR spectroscopy and mass spectrometry.
References
- Larisa V. Zhilitskaya, Nina О. Yarosh, Synthesis of Biologically Active derivatives of 2-Aminobenzothiazole. Russ. Chem. Rev., 2021, Vol. 57, P.369-373.
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