Efficient Regioselective Synthesis of Novel Water-Soluble 2,3-[1,4]thiazino[2,3,4-]quinolin-4-ium Derivatives by Annulation Reactions of 8-quinolinesulfenyl Halides

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2021 Mar 6

PMID 33672444

Citations 2

Authors

Vladimir A Potapov

Roman S Ishigeev

Svetlana V Amosova

Affiliations

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Abstract

Regioselective synthesis of novel 2,3-[1,4]thiazino[2,3,4-]quinolin-4-ium derivatives has been developed by annulation reactions of 8-quinolinesulfenyl halides with vinyl chalcogenides (vinyl ethers, divinyl sulfide, divinyl selenide and phenyl vinyl sulfide) and tetravinyl silane. The novel reagent 8-quinolinesulfenyl bromide was used in the annulation reactions. The influence of the substrate structure and the nature of heteroatoms on the direction of the reactions and on product yields has been studied. The opposite regiochemistry was observed in the reactions with vinyl chalcogenides and tetravinyl silane. The obtained condensed heterocycles are novel water-soluble functionalized compounds with promising biological activity.

Citing Articles

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.

Potapov V, Ishigeev R, Belovezhets L, Amosova S Molecules. 2021; 26(18).

PMID: 34577049 PMC: 8472155. DOI: 10.3390/molecules26185579.

Efficient Regioselective Synthesis of Novel Condensed Sulfur-Nitrogen Heterocyclic Compounds Based on Annulation Reactions of 2-Quinolinesulfenyl Halides with Alkenes and Cycloalkenes.

Potapov V, Ishigeev R, Amosova S Molecules. 2021; 26(16).

PMID: 34443431 PMC: 8399591. DOI: 10.3390/molecules26164844.

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