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

Autor: Obydennik AY; Organic Chemistry Department, Science Faculty, Рeoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation., Titov AA; Organic Chemistry Department, Science Faculty, Рeoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation., Listratova AV; Organic Chemistry Department, Science Faculty, Рeoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation., Borisova TN; Organic Chemistry Department, Science Faculty, Рeoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation., Sokolova IL; Organic Chemistry Department, Science Faculty, Рeoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation., Rybakov VB; Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow, 119991, Russian Federation., Van der Eycken EV; Organic Chemistry Department, Science Faculty, Рeoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation.; Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, 3001, Belgium., Voskressensky LG; Organic Chemistry Department, Science Faculty, Рeoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation., Varlamov AV; Organic Chemistry Department, Science Faculty, Рeoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Jan 11; Vol. 30 (3), pp. e202302919. Date of Electronic Publication: 2023 Nov 20.
DOI: 10.1002/chem.202302919
Abstrakt: 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.)
Databáze: MEDLINE
Externí odkaz: