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. 2024 Jan 11;30(3):e202302919.
doi: 10.1002/chem.202302919. Epub 2023 Nov 20.

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

Arina Y Obydennik  1 , Alexander A Titov  1 , Anna V Listratova  1 , Tatiana N Borisova  1 , Irina L Sokolova  1 , Victor B Rybakov  2 , Erik V Van der Eycken  1   3 , Leonid G Voskressensky  1 , Alexey V Varlamov  1
Affiliations

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

Arina Y Obydennik et al. Chemistry. .

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.

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

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