Synthesis of new polycyclic compounds via the reaction of quinoline-8-sulfenyl halides with cyclic alkenes

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 action of sulfuryl chloride on di(8-quinolinyl) disulfide (2) in methylene chloride or chloroform led to the generation of 8-quinolinesulfenyl chloride (3), which was used in situ without isolation in further reactions with unsaturated heteroatom compounds (Scheme 2). Despite some progress in the development of synthetic methods for the preparation of 2H,3H- [1,4]thiazino [2,3,4-ij]quinolin-4-ium derivatives [33][34][35][36][37][38][39][40][41], the annulation reactions of 8-quinolinesulfenyl halides with a number of vinylic heteroatom compounds (4-pentenoic acid, 5-hexenoic acid, allyl chloride and bromide, allyl cyanate, N-vinyl pyrrolidin-2-one, 1-vinylimidazole, ethyl and butyl vinyl ethers) have not been described in the literature. The synthesis of novel families of compounds with potential biological activity and evaluation of their antimicrobial properties represent urgent tasks.…”

“…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 2Н,3Н- [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)-2Н,3Н- [1,4]thiazino [2,3,4-ij]quinolin-4-ium chloride (1) (Scheme 1).…”

“…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 2Н,3Н- [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)-2Н,3Н- [1,4]thiazino [2,3,4- Despite some progress in the development of synthetic methods for the preparation of 2H,3H- [1,4]thiazino [2,3,4-ij]quinolin-4-ium derivatives [33][34][35][36][37][38][39][40][41], the annulation reactions of 8-quinolinesulfenyl halides with a number of vinylic heteroatom compounds (4-pentenoic acid, 5-hexenoic acid, allyl chloride and bromide, allyl cyanate, N-vinyl pyrrolidin-2-one, 1-vinylimidazole, ethyl and butyl vinyl ethers) have not been described in the literature.…”

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

“…The reactions of 8-quinolinesulfenyl halides with cycloalkenes (cyclopentene, cyclohexene and cyclooctene), depending on the nature of the halogen, led to [1,4]thiazino[2,3,4- ij ]quinolin-11-ium derivatives or 8-[(2-chlorocycloalkyl)sulfanyl]quinolines in high yields (90–100%) ( Scheme 2 ). The reactions of 8-quinolinesulfenyl chloride with cycloalkenes led to electrophilic addition products, while condensed compounds were obtained in the case of 8-quinolinesulfenyl bromide ( Scheme 2 ) [ 41 ].…”