Intramolecular [4+2] cycloaddition of furfurylsubstituted homoallylamines to allylhalides, acryloyl chloride and maleic anhydride

Acylation of 4-(furyl-2)-4-R-aminobut-1-enes and 4-R-4-furfurylaminobut-1- enes with maleic anhydride, acryloyl chloride or allylhalides provided 3-aza-10-oxatricyclo[5.2.1.01.5]decenes. The tricycles are formed via an initial amide formation followed by a stereoselective exo-IMDAF (Intramolecular Diels-Alder of Furan). In case of competing cycloaddition (for compounds possessing two furan or two dienophilic moieties) the most substituted fivemembered cycle is preferably annulated. Refluxing of 4-R-4- furfurylaminobut-1-enes in acetic anhydride led to exo-3-aza-11-oxatricyclo[6.2. 1.01.6]undecenes with the pseudoequatorial substituent R-4. Treatment of 3-aza-10-oxatricyclo[5.2.1.01.5]decenes with PPA at 90-110 °C promoted cyclic ether opening, aromatization and intramolecular cyclization reactions sequence to give the corresponding tetracyclic compounds - tetrahydroisoindolo[2,1-a]quinolines and tetrahydroisoindolo[2,1-b][2] benzazepines in good yields. Unusual products of ipso-substitution in aromatic ring were obtained on cyclization of N-p-R-substituted 2-allyl-4-oxo-3-aza-10- oxatricyclo[5.2.1.01.5]dec-8-enes.

Авторы
Varlamov A.V. 1 , Boltukhina E.V. 1 , Zubkov F.I. 1 , Nikitina E.V. 1 , Turchin K.F.2
Редакторы
-
Издательство
HeteroCorporation
Номер выпуска
6
Язык
Английский
Страницы
1479-1495
Статус
Опубликовано
Подразделение
-
Номер
-
Том
43
Год
2006
Организации
  • 1 Organic Chemistry Department, Russian Peoples' Friendship University, 6, Miklukho-Maklayia St., Moscow 117198, Russian Federation
  • 2 Center of Drugs Chemistry, All-Russian Institute for Chemical and Pharmaceutical Research, 7, Zubovskaya St., Moscow 119815, Russian Federation
Ключевые слова
3 aza 10 oxatricyclo[6.2.1.0]undecene derivative; 3 aza 11 oxatricyclo[6.2.1.0]undecene derivative; acrylic acid derivative; acryloyl chloride; allylhalide derivative; amine; furan; furan derivative; halide; homoallylamine derivative; maleic anhydride; quinoline derivative; tetrahydroisoindolo[2,1 a]quinoline derivative; undecanol; acylation; aromatization; article; cyclization; cycloaddition; Diels Alder reaction; product recovery; reaction analysis; sequence analysis; stereochemistry; substitution reaction
Дата создания
19.10.2018
Дата изменения
19.10.2018
Постоянная ссылка
https://repository.rudn.ru/ru/records/article/record/3321/