New reactions of 3,4‐dihydro‐6,7‐dimethoxyisoquinoline ylide with nitrile derivatives

Novel examples for dipolar cycloaddition of isoquinolinium ylides to nitriles leading to new imidazo[2,1‐a]isoquinolines were described and the potential of this reaction in synthetic chemistry was explored. As a by‐product of this research, a number of N‐substituted, 3,4‐dihydro‐1H‐isoquinoline‐1‐c...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 59; no. 9; pp. 1635 - 1650
Main Authors Molnár, Márk, Treuerne Balázs, Krisztina E., Madarász, Zoltán, Nyerges, Miklós
Format Journal Article
LanguageEnglish
Published Chichester, UK John Wiley & Sons, Inc 01.09.2022
Wiley
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Subjects
Bromides
Chemistry
Chemistry, Organic
Cycloaddition
Nitriles
Physical Sciences
Science & Technology
Triethylamine
1,3-DIPOLAR CYCLOADDITIONS
IMIDAZOLE DERIVATIVES
CYANOFORMATE
ALPHA
CYANATION
3+2 CYCLOADDITION REACTIONS
TRIMETHYLSILYL CYANIDE
STRECKER REACTION
ACCESS
CYANOHYDRIN
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Summary:Novel examples for dipolar cycloaddition of isoquinolinium ylides to nitriles leading to new imidazo[2,1‐a]isoquinolines were described and the potential of this reaction in synthetic chemistry was explored. As a by‐product of this research, a number of N‐substituted, 3,4‐dihydro‐1H‐isoquinoline‐1‐carbonitriles were synthesized by a simple, efficient reaction of a series of isoquinolinium bromides and ethyl cyanoformate in the presence of triethylamine. First examples of 1,3‐dipolar cycloaddition of isoquinolinium ylides to nitriles leading to new imidazo[2,1‐a]isoquinolines are described. The reaction with ethyl cyanoformate gave N‐substituted, 3,4‐dihydro‐1H‐isoquinoline‐1‐carbonitriles as a sole product.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4496