[3+2] ANNULATION OF 2-SUBSTITUTED 3-NITRO-2<i>H</i>-CHROMENES WITH MERCAPTOACETALDEHYDE: STEREOSELECTIVE SYNTHESIS OF TETRAHYDRO-4<i>H</i>-THIENO[3,2-<i>c</i>]CHROMEN-3-OLS

Authors

  • Алексей Ю. Барков Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
  • Иван А. Кочнев Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
  • Никита С. Симонов Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
  • Игорь Б. Кутяшев Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
  • Николай С. Зимницкий Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
  • Владислав Ю. Коротаев Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia
  • Вячеслав Я. Сосновских Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia

DOI:

https://doi.org/10.1007/6427

Keywords:

2, 5-dihydroxy-1, 4-dithiane, 3-nitro-2H-chromenes, tetrahydrothieno[3, 2-c]chromen-3-ols, intramolecular Henry reaction, thia-Michael reaction.

Abstract

A diastereoselective method was developed for the synthesis of 4-trifluoromethyl- and 4-phenyl-substituted 3a-nitro-2,3,3a,9b-tetrahydro-4H-thieno[3,2-c]chromen-3-ols having cis configuration of substituents at the C-3, C-3a, C-4 atoms and the 9b-CH hydrogen atom from the available starting materials – 3-nitro-2H-chromenes and 2,5-dihydroxy-1,4-dithiane in 80–92% yields. This approach relied on a tandem of Michael and Henry reactions between 3-nitro-2H-chromenes and in situ generated mercaptoacetaldehyde in Et2O at room temperature over 4–6 h, using Et3N as catalyst.

 

Author Biography

Владислав Ю. Коротаев, Institute of Natural Sciences and Mathematics, Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenina Ave., Yekaterinburg 620000, Russia

кафедра органической химии и высокомолекулярных соединений, д.х.н.

Published

2021-12-15

Issue

Section

Original Papers