Open Access Open Access  Restricted Access Subscription Access

SYNTHESIS OF NEW POLYCYCLIC COMPOUNDS via THE REACTION OF QUINOLINE-8-SULFENYL HALIDES WITH CYCLIC ALKENES

Роман С. Ишигеев, Владимир А. Потапов, Ирина В. Шкурченко, Альфия Г. Хабибулина, Светлана В. Амосова
Cover Image

Abstract


The reactions of quinoline-8-sulfenyl 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%). The annulation reactions of quinoline-8-sulfenyl halides with 3,4-dihydro-2H-pyran proceed regioselectively with the formation of the condensed compounds in quantitative yield. For the first time, the possibility of use and efficiency of a previously unknown quinoline-8-sulfenyl bromide in annulation reactions has been demonstrated. When quinoline-8-sulfenyl halides react with 2,5-dihydrofuran, the products of electrophilic addition are formed.

 


Keywords


cyclopentene; 8,8'-disulfanediyldiquinoline; quinoline-8-sulfenyl bromide; quinoline-8-sulfenyl chloride; [1,4]thiazino[2,3,4-ij]-quinolin-11-ium derivatives.

Full Text: PDF (Russian) Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv