EFFECTIVE SYNTHESIS OF HARD-TO-REACH 3,4-DISUBSTITUTED THIOPHENE DERIVATIVES BASED ON BIS(2-CHLOROPROPENYL) SULFIDE

Authors

  • Валентина С. Никонова Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia
  • Николай А. Корчевин Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia
  • Татьяна Н. Бородина Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia
  • Владимир И. Смирнов Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia
  • Александр И. Албанов Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia
  • Игорь Б. Розенцвейг Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russia

DOI:

https://doi.org/10.1007/5859

Keywords:

4-(hydroxymethyl)thiophene-3-carbaldehyde, 4, 5, 9, 10-tetrahydrothieno[3', 6]cycloocta[1, 2-c]thiophene, 1H, 4H-thieno- [3, 4-d][1, 2]dioxine, thiophenes.

Abstract

An efficient approach for the synthesis of hard-to-reach 3,4-disubstituted thiophene derivatives: 4,5,9,10-tetrahydrothieno[3',4;5,6]cycloocta[1,2-c]thiophene, 1H,4H-thieno[3,4-d][1,2]dioxine, 4-(hydroxymethyl)thiophene-3-carbaldehyde, based on consecutive transformations of bis(2-chloropropenyl) sulfide has been found. Transformations were realized without isolation of the intermediate compounds. The reactivity of 4,5,9,10-tetrahydrothieno[3',4;5,6]cycloocta[1,2-c]thiophene has been studied based on the example of acetylation reaction, and the possibility of obtaining bifunctional derivatives with the participation of both thiophene rings has been
shown. The structure of some synthesized compounds has been studied with X-ray diffraction method.

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Published

2020-11-05

Issue

Vol. 56 No. 10 (2020)

Section

Original Papers