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

Obydennik, Arina Y; Titov, Alexander A; Listratova, Anna V; Borisova, Tatiana N; Sokolova, Irina L; Rybakov, Victor B; Van der Eycken, Erik V; Voskressensky, Leonid G; Varlamov, Alexey V

Obydennik, Arina Y; Titov, Alexander A; Listratova, Anna V; Borisova, Tatiana N; Sokolova, Irina L; Rybakov, Victor B; Van der Eycken, Erik V; Voskressensky, Leonid G; Varlamov, Alexey V.

Afiliação

Obydennik AY; Organic Chemistry Department, Science Faculty, Ð eoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation.
Titov AA; Organic Chemistry Department, Science Faculty, Ð eoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation.
Listratova AV; Organic Chemistry Department, Science Faculty, Ð eoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation.
Borisova TN; Organic Chemistry Department, Science Faculty, Ð eoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation.
Sokolova IL; Organic Chemistry Department, Science Faculty, Ð eoples' 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, Ð eoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation.
Voskressensky LG; Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, 3001, Belgium.
Varlamov AV; Organic Chemistry Department, Science Faculty, Ð eoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation.

Chemistry ; 30(3): e202302919, 2024 Jan 11.

Article em En | MEDLINE | ID: mdl-37864779

ABSTRACT

ABSTRACT

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.

Palavras-chave

microwave irradiation; pyrido[2,1-a]isoquinolines; pyrrolo[2,1-a]isoquinolines; pyrrolo[2,1-b][3]benzazepines; sigmatropic rearrangement

Texto completo

Adicionar na Minha BVS

Imprimir

XML

PubMed Links

Buscar no Google

Texto completo: 1 Bases de dados: MEDLINE Idioma: En Revista: Chemistry Assunto da revista: QUIMICA Ano de publicação: 2024 Tipo de documento: Article