SYNTHESIS OF SPIRO[IMIDAZOLE-4,3'-QUINOLIN]ONES FROM [2-(DIMETHYLAMINO)BENZYLIDENE]-2-(METHYLSULFANYL)IMIDAZOLONES

Authors

  • Эльвира Р. Зайцева D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow 125047, Russia Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia
  • Александр Ю. Смирнов Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia N. I. Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997, Russia
  • Надежда С. Балеева Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia N. I. Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997, Russia
  • Михаил С. Баранов Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia N. I. Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997, Russia

DOI:

https://doi.org/10.1007/6174

Keywords:

2-(methylsulfanyl)imidazolones, quinolines, spirocyclic compounds, [1, 5]-hydride shift.

Abstract

The treatment of 5-[2-(dimethylamino)benzylidene]-3-methyl-2-(methylsulfanyl)-3,5-dihydro-4H-imidazol-4-ones with catalytic amounts of scandium triflate resulted in a [1,5]-hydride shift followed by cyclization, giving 1,1'-dimethyl-2-(methylsulfanyl)-1',4'-dihydro-2'H-spiro[imidazole-4,3'-quinolin]-5(1H)-ones. All of the newly synthesized compounds containing various substituents in the benzylidene moiety were isolated in good yields.

Author Biographies

Эльвира Р. Зайцева, D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow 125047, Russia Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia

Группа химии гетероциклических соединений

 

Александр Ю. Смирнов, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia N. I. Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997, Russia

Группа химии гетероциклических соединений

Надежда С. Балеева, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia N. I. Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997, Russia

Группа химии гетероциклических соединений

Михаил С. Баранов, Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St., Moscow 117997, Russia N. I. Pirogov Russian National Research Medical University, 1 Ostrovityanova St., Moscow 117997, Russia

Группа химии гетероциклических соединений

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Published

2021-06-19

Issue

Vol. 57 No. 6 (2021)

Section

Short Communications