CuCN-Catalyzed Synthesis of 11-R1-5,6-Dihydro-1H-pyrrolo[2,1-b][3]benzazepines from 1-R1-1-Ethynyl-2-vinyl-1,2,3,4-tetrahydroisoquinolines

A two-step protocol, involving Michael addition with following C-1 alkynylation of readily available 1-R1-substituted tetrahydroisoquinolines with methyl propiolate and CuCN-mediated intramolecular cyclization, was employed to obtain 11-R1-substituted 1H-pyrrolo[2,1-b][3]benzazepines. A method for converting 1H-pyrrolo[2,1-b][3]benzazepines into their structural isomers has been developed. © 2025 Elsevier B.V., All rights reserved.

Авторы
Obydennik Arina Y. 1 , Titov Alexander A. 1 , Borisova Tatiana N. 1 , Voskressensky Leonid G. 1 , Varlamov Alexey V. 1
Journal
Journal of Organic Chemistry
Издательство
American Chemical Society
Номер выпуска
35
Язык
English
Страницы
12490-12495
Статус
Published
Ссылка
Внешняя ссылка
DOI
10.1021/ACS.JOC.5C01327
Том
90
Год
2025
Организации
  • 1 Department of Organic Chemistry, RUDN University, Moscow, Russian Federation
Ключевые слова
Addition reactions; Copper compounds; Plants (botany); Synthesis (chemical); Alkynylations; Catalyzed synthesis; Ethynyl; Intramolecular cyclizations; Michael additions; Structural isomers; Tetrahydroisoquinolines; Two-step protocol; Isomers; 5,6 dihydro 1 h pyrrolo[2,1 b ][3]benzazepine derivative; benzazepine derivative; copper; cyanide; tetrahydroisoquinoline derivative; unclassified drug; alkynylation; Article; carbon nuclear magnetic resonance; catalysis; chemical modification; controlled study; cyclization; electrospray; environmental temperature; Fourier transform infrared spectroscopy; heteronuclear multiple bond correlation; heteronuclear multiple quantum coherence; isomer; Michael addition; microwave irradiation; nuclear Overhauser effect; nucleophilicity; proton nuclear magnetic resonance; reaction analysis; reaction time; rearrangement reaction; structure analysis; substitution reaction; synthesis; thin layer chromatography
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