A New Approach to the Synthesis of Quinolyzinium Salts Based on N-(4,4-Dibromobut-2-en-1-yl)-Substituted Pyridines

A variety of N-allyl substituted pyridinium salts based on 1-(Z)-(1,4,4-tribromobut-2-en-2-yl)adamantane were synthesized. It was found that under the action of triethylamine on allyl substituted salts, deprotonation occurs, followed by the elimination of the bromide anion to form a new pyridinium salt of the diene structure. Further, a variety of quinolyzinium salts were obtained as a result of thermal 6π-electrocyclization of dienic salts.

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Journal
Russian Journal of General Chemistry
Published
2026-02-01
DOI
https://doi.org/10.1134/s1070363225606076
Primary Topic
Synthesis and Reactivity of Heterocycles
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article
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article

A New Approach to the Synthesis of Quinolyzinium Salts Based on N-(4,4-Dibromobut-2-en-1-yl)-Substituted Pyridines

M. R. Baimuratov, Anastasiya N. Bogdanova, М. В. Леонова, Yu. N. Klimochkin et al.
Russian Journal of General Chemistry
Synthesis and Reactivity of Heterocycles
article

A New Approach to the Synthesis of Quinolyzinium Salts Based on N-(4,4-Dibromobut-2-en-1-yl)-Substituted Pyridines

M. R. Baimuratov, Anastasiya N. Bogdanova, М. В. Леонова, Yu. N. Klimochkin, O. A. Lodochnikova, Ivan A. Anuriev
article en

Abstract

A variety of N-allyl substituted pyridinium salts based on 1-(Z)-(1,4,4-tribromobut-2-en-2-yl)adamantane were synthesized. It was found that under the action of triethylamine on allyl substituted salts, deprotonation occurs, followed by the elimination of the bromide anion to form a new pyridinium salt of the diene structure. Further, a variety of quinolyzinium salts were obtained as a result of thermal 6π-electrocyclization of dienic salts.

Russian Journal of General ChemistryVol. 96(2)
Samara State Technical University (RU), A.E. Arbuzov Institute of Organic and Physical Chemistry (RU)
Clean water and sanitation
Openalex Percentile: Top 61%
Synthesis and Reactivity of Heterocycles
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