A Novel Family of [1,4]Thiazino[2,3,4-]quinolin-4-ium Derivatives: Regioselective Synthesis Based on Unsaturated Heteroatom and Heterocyclic Compounds and Antibacterial Activity

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2021 Sep 28

PMID 34577049

Authors

Vladimir A Potapov

Roman S Ishigeev

Lyudmila A Belovezhets

Svetlana V Amosova

Affiliations

Soon will be listed here.

Abstract

A novel family of [1,4]thiazino[2,3,4-]quinolin-4-ium derivatives was synthesized by annulation reactions of 8-quinolinesulfenyl chloride with unsaturated heteroatom and heterocyclic compounds. It was found that the reactions with 4-pentenoic and 5-hexenoic acids, allyl chloride and bromide, allyl cyanate and vinyl heterocyclic compounds (-vinyl pyrrolidin-2-one and 1-vinylimidazole) proceeded in a regioselective mode but with the opposite regiochemistry. The reactions with vinyl heterocyclic compounds included electrophilic addition of the sulfur atom of 8-quinolinesulfenyl chloride to the β-carbon atom of the vinyl group. In the case of other substrates, the annulation proceeded with the attachment of the sulfur atom to the α-carbon atom of the vinyl group. The antibacterial activity of novel water-soluble compounds against , and was evaluated. Compounds with high antibacterial activity were found.

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