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

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.

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

“…Recently we described the annulation reactions of 8-quinolinesulfenyl halides with vinylic heteroatom compounds, including vinylic ethers, sulfides, divinyl selenide and tetravinyl silane [ 40 ]. Starting 8-quinolinesulfenyl halides were generated in situ from di(8-quinolinyl) disulfide by the action of sulfuryl chloride or bromine and used in further reactions without isolation ( Scheme 1 ).…”

“…The annulation reactions of 8-quinolinesulfenyl halides with vinylic ethers, sulfides and divinyl selenide proceeded in a regioselective manner affording 3-substituted 2 H ,3 H -[1,4]thiazino[2,3,4- ij ]quinolin-4-ium halides in high yields ( Scheme 1 ) [ 40 ]. The annulation reaction of 8-quinolinesulfenyl halides with tetravinyl silane was found to occur with opposite regiochemistry leading to 2-trivinylsilyl-2 H ,3 H -[1,4]thiazino[2,3,4- ij ]quinolin-4-ium halides in near quantitative yields ( Scheme 1 ).…”

“…The aim of this research is the development of the efficient regioselective synthesis of novel condensed [1,3]thiazolo[3,2- a ]quinolin-10-ium derivatives with promising biological activity based on annulation reactions of 2-quinolinesulfenyl halides with alkenes and cycloalkenes. The annulation of 5-membered 1,3-thiazole heterocycle to the quinoline ring occurs in the reaction of 2-quinolinesulfenyl halides with alkenes and cycloalkenes, whereas the annulation of 6-membered 1,4-thiazine heterocycle to the quinoline ring is observed in the reactions of 8-quinolinesulfenyl halides with cycloalkenes and vinyl heteroatom compounds [ 40 , 41 ] ( Scheme 1 and Scheme 2 ).…”

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

“…The development of a method for the efficient regioselective synthesis of novel heterocyclic and condensed organochalcogen compounds by cyclization and annulation reactions of chalcogen reagents is the focus of our research [21][22][23][24][25][26][27][28][29][30][31][32][33][34]. Recently we described the annulation reactions of 8-pyridinesulfenyl halides with functionalized alkenes and cycloalkenes affording a series of 2H,3H- [1,4]thiazino [2,3,4-ij]quinolin-4-ium derivatives in high yields [33,34].…”

“…The development of a method for the efficient regioselective synthesis of novel heterocyclic and condensed organochalcogen compounds by cyclization and annulation reactions of chalcogen reagents is the focus of our research [21][22][23][24][25][26][27][28][29][30][31][32][33][34]. Recently we described the annulation reactions of 8-pyridinesulfenyl halides with functionalized alkenes and cycloalkenes affording a series of 2H,3H- [1,4]thiazino [2,3,4-ij]quinolin-4-ium derivatives in high yields [33,34]. For example, the annulation reactions with divinyl and vinyl phenyl sulfides proceeded with the attachment of the sulfur atom of 8-pyridinesulfenyl halides at the β-position of the vinylsulfanyl group, while the addition of the sulfur atom occurred at the α-carbon atom of the vinylsilyl moiety in the case of tetravinyl silane with the formation of 2-(trivinylsilyl)-2H,3H- [1,4]thiazino [2,3,4-ij]quinolin-4-ium chloride (1) (Scheme 1).…”