5-amido- and 5-amino-substituted epoxyisoindolo[2,1-a]tetrahydroquinolines and 10-carboxylic acids: Their synthesis and reactivity

The interactions between 4-R-substituted 2-furyl-1,2,3,4- tetrahydroquinolines (synthesized by the Povarov reaction) and a number of alkenes have been investigated. Maleic, dibromomaleic, dichloromaleic, and citraconic anhydrides, as well as acryloyl, methacryloyl, crotonyl, and cynnamoyl chlorides were used as alkene components. It was shown that the initial N-acylation of the tetrahydroquinolines was followed by a spontaneous [4+2]-cycloaddition of an N-acryloyl substituent to the furan ring. It was established that the intramolecular Diels-Alder reaction of furans is reversible, occurs stereoselectively as exo-addition, and led to target epoxyisoindolo[2,1-a]tetrahydroquinolines with moderate yields. Oxidation and aromatization of the synthesized products were carried out. © 2013 HeteroCorporation.

Издательство
HeteroCorporation
Номер выпуска
SUPPL.1
Язык
Английский
Страницы
E18-E38
Статус
Опубликовано
Том
50
Год
2013
Организации
  • 1 Department of Organic Chemistry, Peoples' Friendship University of Russia, 6 Miklukho-Maklaya St., Moscow 117198, Russian Federation
  • 2 Department of Chemistry, University of Douala, Faculty of Sciences, PO Box 24157, Douala, Cameroon
  • 3 Valeant Canada Ltd., 1956 Bourdon St., Montréal, QC H4M 1V1, Canada
Ключевые слова
alkene derivative; carboxylic acid derivative; maleic acid derivative; quinoline derivative; acylation; aromatization; article; chemical interaction; chemical structure; cycloaddition; electron; esterification; nuclear Overhauser effect; oxidation; proton nuclear magnetic resonance; stereochemistry; synthesis; thermodynamics
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/2128/