SYNTHESIS OF 3-AMINO-6,7-DIHYDROFERROCENO[<i>a</i>]QUINOLIZIN-4-ONE DERIVATIVES <i>VIA</i> THE REACTION OF 3,4-DIHYDROFERROCENO[<i>c</i>]PYRIDINES WITH AZLACTONES

Authors

  • Владислав Ю. Шувалов Omsk State Technical University, 11 Mira Ave., Omsk 644050, Russia
  • Юлия С. Рожкова Institute of Technical Chemistry, Ural Branch of the Russian Academy of Sciences, 3 Akademika Koroleva St., Perm 614013, Russia
  • Ирина В. Плеханова Institute of Technical Chemistry, Ural Branch of the Russian Academy of Sciences, 3 Akademika Koroleva St., Perm 614013, Russia
  • Анастасия С. Костюченко Omsk State Technical University, 11 Mira Ave., Omsk 644050, Russia
  • Юрий В. Шкляев Institute of Technical Chemistry, Ural Branch of the Russian Academy of Sciences, 3 Akademika Koroleva St., Perm 614013, Russia
  • Александр С. Фисюк Omsk State Technical University, 11 Mira Ave., Omsk 644050, Russia Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia

DOI:

https://doi.org/10.1007/6505

Keywords:

3-amino-4-arylpyridin-2(1H)-one, 3-amino-6, 7-dihydroferroceno[a]quinolizin-4-one, azlactone, 3, 4-dihydroferroceno[c]pyridine, ferrocene, oxidation, tautomerism.

Abstract

Derivatives of 3-amino-6,7-dihydroferroceno[a]quinolizin-4-one were obtained by the reaction of 3,4-dihydroferroceno[c]pyridines with 4-(ethoxymethylidene)- and 4-(3-oxo-2-benzofuran-1(3H)-ylidene)-2-phenyl-1,3-oxazol-5(4H)-ones (azlactones) in moderate to good yields. The intermediate products of the addition of 4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5(4H)-one to the alkyl group of 1-alkyl-3,4-dihydroferroceno[c]pyridines were isolated and characterized. The reaction of 4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one with 3,4-dihydroferroceno[c]pyridines led to the formation of derivatives of 3-amino-2-phenyl-3,4,6,7-tetrahydroferroceno[a]quinolizin-4-one, which were oxidized with DDQ to 3-amino-2-phenyl-6,7-dihydroferroceno[a]quinolizin-4-one.

Author Biography

Александр С. Фисюк, Omsk State Technical University, 11 Mira Ave., Omsk 644050, Russia Dostoevsky Omsk State University, 55a Mira Ave., Omsk 644077, Russia

Заведующий кафедрой органической химии ОмГУ им. Ф.М. Достоевского, заведующий лабораторией "Новые органические материалы" ОмГТУ, д.х.н., профессор.

Published

2022-01-27

Issue

Section

Original Papers