Divergent and Nucleophile-Assisted Rearrangement in the Construction of Pyrrolo[2,1-b][3]benzazepine and Pyrido[2,1-a]isoquinoline Scaffolds

Under microwave (MW) irradiation at 150 °C in toluene and in the presence of nucleophiles (DMAP, triphenylphosphine and tetrahydrothiophene) 1-substituted 1-ethynyl-2-vinyldi- and tetrahydroisoquinolines undergo [3,3]-sigmatropic rearrangement providing pyrrolo[2,1-b][3]benzazepines in good yields. The replacement of toluene with acetonitrile directs the rearrangement towards the formation of 7,11b-dihydro-6H-pyrido[2,1-a]isoquinolines. © 2023 Wiley-VCH GmbH.

Авторы
Obydennik A.Y. , Titov A.A. , Listratova A.V. , Borisova T.N. , Sokolova I.L. , Rybakov V.B. , Van der Eycken E.V. , Voskressensky L.G. , Varlamov A.V.
Журнал
Chemistry - A European Journal
Издательство
Wiley-VCH Verlag
Номер выпуска
3
Язык
Английский
Статус
Опубликовано
Ссылка
Внешняя ссылка
DOI
10.1002/CHEM.202302919
Номер
e202302919
Том
30
Год
2024
Организации
  • 1 Organic Chemistry Department, Science Faculty, Рeoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation
  • 2 Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1–3, Moscow, 119991, Russian Federation
  • 3 Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, 3001, Belgium
Ключевые слова
microwave irradiation; pyrido[2,1-a]isoquinolines; pyrrolo[2,1-a]isoquinolines; pyrrolo[2,1-b][3]benzazepines; sigmatropic rearrangement
Цитировать
ГОСТ MLA RIS BibTex
Поделиться

Другие записи