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

Vladimir A Potapov; Roman S Ishigeev; Svetlana V Amosova

doi:10.3390/molecules26164844

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

Molecules. 2021 Aug 10;26(16):4844. doi: 10.3390/molecules26164844.

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

The preparation of novel reagents 2-quinolinesulfenyl chloride and bromide based on available 2-mercaptoquinoline has been described. This approach opens up opportunities for the introduction of 2-quinolinesulfenyl chloride and bromide into organic synthesis. Regioselective synthesis of novel 1,2-dihydro[1,3]thiazolo[3,2-a]quinolin-10-ium derivatives in high yields has been developed by annulation reactions of 2-quinolinesulfenyl chloride and bromide with alkenes. Condensed tetracyclic products have been obtained by the reactions of 2-quinolinesulfenyl chloride and bromide with cycloalkenes. The opposite regiochemistry in the reactions with styrene, isoeugenol and 1-alkenes was discussed.

Keywords: 1,2-dihydro[1,3]thiazolo[3,2-a]quinolin-10-ium derivatives; 2-mercaptoquinoline; 2-quinolinesulfenyl bromide; 2-quinolinesulfenyl chloride; alkenes; annulation reactions; cycloalkenes.