Home / Publications / Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1',2':3,4]imidazo[2,1-a]isoquinolines

Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1',2':3,4]imidazo[2,1-a]isoquinolines

, 
Lina Pavlovna Nikitina 1
Lina Pavlovna Nikitina
, 
Ivan Vladimirovich Saliy 1
Ivan Vladimirovich Saliy
, 
Veronika Sergeevna Saliy 1
Veronika Sergeevna Saliy
, 
Andrei Valer'evich Afonin 1
Andrei Valer'evich Afonin
, 
Ludmila Andreevna Oparina 1
Ludmila Andreevna Oparina
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2024.09.021
Published 2024-09-09
Communication , Volume 34, Issue 5, 691-693
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Belyaeva K. V. et al. Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1',2':3,4]imidazo[2,1-a]isoquinolines // Mendeleev Communications. 2024. Vol. 34. No. 5. pp. 691-693.
GOST all authors (up to 50) Copy
Belyaeva K. V., Nikitina L. P., Saliy I. V., Saliy V. S., Afonin A. V., Oparina L. A., Trofimov B. A. Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1',2':3,4]imidazo[2,1-a]isoquinolines // Mendeleev Communications. 2024. Vol. 34. No. 5. pp. 691-693.
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TY - JOUR
DO - 10.1016/j.mencom.2024.09.021
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.09.021
TI - Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1',2':3,4]imidazo[2,1-a]isoquinolines
T2 - Mendeleev Communications
AU - Belyaeva, Kseniya Vasil'evna
AU - Nikitina, Lina Pavlovna
AU - Saliy, Ivan Vladimirovich
AU - Saliy, Veronika Sergeevna
AU - Afonin, Andrei Valer'evich
AU - Oparina, Ludmila Andreevna
AU - Trofimov, Boris Aleksandrovich
PY - 2024
DA - 2024/09/09
PB - Mendeleev Communications
SP - 691-693
IS - 5
VL - 34
ER -
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@article{2024_Belyaeva,
author = {Kseniya Vasil'evna Belyaeva and Lina Pavlovna Nikitina and Ivan Vladimirovich Saliy and Veronika Sergeevna Saliy and Andrei Valer'evich Afonin and Ludmila Andreevna Oparina and Boris Aleksandrovich Trofimov},
title = {Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1',2':3,4]imidazo[2,1-a]isoquinolines},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.09.021},
number = {5},
pages = {691--693},
doi = {10.1016/j.mencom.2024.09.021}
}
MLA
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Belyaeva, Kseniya Vasil'evna, et al. “Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1',2':3,4]imidazo[2,1-a]isoquinolines.” Mendeleev Communications, vol. 34, no. 5, Sep. 2024, pp. 691-693. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.09.021.

Keywords

alkyne
Annulation
isoquinoline
Pyrrole
zwitteriones.

Abstract

1-Methylisoquinoline undergoes stereoselective annulation with pyrrolylacetylenic ketones (MeCN, 80-82 °C) to provide (E)-acylethenylpyrrolo[1’,2’:3,4]imidazo[2,1-a]isoquinolines in up to 92% yield. In the case of 5-arylpyrrolylacetylenic ketones, instead of the above cyclization, the dimerization of the starting ketones to give dipyrrolopyrazines in 38 and 39% yields occurs.

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