SYNTHESIS OF NEW POLYCYCLIC COMPOUNDS <i>v</i>ia THE REACTION OF QUINOLINE-8-SULFENYL HALIDES WITH CYCLIC ALKENES

Authors

  • Роман С. Ишигеев A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia
  • Владимир А. Потапов A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia
  • Ирина В. Шкурченко A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia Pedagogical Institute of Irkutsk State University, 6 Nizhnyaya Naberezhnaya St., Irkutsk 664003, Russia
  • Альфия Г. Хабибулина A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia
  • Светлана В. Амосова A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia

DOI:

https://doi.org/10.1007/6112

Keywords:

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

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.

 

Author Biographies

Роман С. Ишигеев, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia

к.х.н., научный сотрудник лаборатории
халькогенорганических соединений
Иркутского института химии им. А. Е. Фаворского CО РАН

Владимир А. Потапов, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia

д.х.н., профессор, зав. лабораторией халькогенорганических соединений Иркутского института химии им. А. Е. Фаворского CО РАН

Ирина В. Шкурченко, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia Pedagogical Institute of Irkutsk State University, 6 Nizhnyaya Naberezhnaya St., Irkutsk 664003, Russia

к.х.н., научный сотрудник лаборатории
халькогенорганических соединений
Иркутского института химии им. А. Е. Фаворского CО РАН

Альфия Г. Хабибулина, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia

к.х.н., научный сотрудник лаборатории
халькогенорганических соединений
Иркутского института химии им. А. Е. Фаворского CО РАН

Светлана В. Амосова, A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia

д.х.н., главный научный сотрудник лаборатории
халькогенорганических соединений
Иркутского института химии им. А. Е. Фаворского CО РАН

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Published

2021-03-15

Issue

Vol. 57 No. 3 (2021)

Section

Original Papers