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

Vladimir A Potapov; Roman S Ishigeev; Svetlana V Amosova

doi:10.3390/molecules26041116

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

Molecules. 2021 Feb 20;26(4):1116. doi: 10.3390/molecules26041116.

Authors

Vladimir A Potapov¹, Roman S Ishigeev¹, Svetlana V Amosova¹

Affiliation

¹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia.

Abstract

Regioselective synthesis of novel 2H,3H-[1,4]thiazino[2,3,4-ij]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.

Keywords: 2H,3H-[1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives; 8-quinolinesulfenyl halides; annulation reactions; divinyl selenide; divinyl sulfide; phenyl vinyl sulfide; tetravinyl silane; vinyl ethers.

MeSH terms

Molecular Structure
Quinolinium Compounds / chemical synthesis*
Quinolinium Compounds / chemistry
Solubility
Stereoisomerism
Water / chemistry

Substances

Quinolinium Compounds
Water