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Cyanoacetylene-driven base catalyzed synthesis of dihydropyrimidophenanthridinones from phenanthridine and water

, 
Lina Pavlovna Nikitina 1
Lina Pavlovna Nikitina
, 
Anastasiya Grigor'evna Mal'kina 1
Anastasiya Grigor'evna Mal'kina
, 
Andrei Valer'evich Afonin 1
Andrei Valer'evich Afonin
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2020.01.004
Published 2019-12-30
Communication , Volume 30, Issue 1, 12-14
4
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Belyaeva K. V. et al. Cyanoacetylene-driven base catalyzed synthesis of dihydropyrimidophenanthridinones from phenanthridine and water // Mendeleev Communications. 2019. Vol. 30. No. 1. pp. 12-14.
GOST all authors (up to 50) Copy
Belyaeva K. V., Nikitina L. P., Mal'kina A. G., Afonin A. V., Trofimov B. A. Cyanoacetylene-driven base catalyzed synthesis of dihydropyrimidophenanthridinones from phenanthridine and water // Mendeleev Communications. 2019. Vol. 30. No. 1. pp. 12-14.
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TY - JOUR
DO - 10.1016/j.mencom.2020.01.004
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.004
TI - Cyanoacetylene-driven base catalyzed synthesis of dihydropyrimidophenanthridinones from phenanthridine and water
T2 - Mendeleev Communications
AU - Belyaeva, Kseniya Vasil'evna
AU - Nikitina, Lina Pavlovna
AU - Mal'kina, Anastasiya Grigor'evna
AU - Afonin, Andrei Valer'evich
AU - Trofimov, Boris Aleksandrovich
PY - 2019
DA - 2019/12/30
PB - Mendeleev Communications
SP - 12-14
IS - 1
VL - 30
ER -
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@article{2019_Belyaeva,
author = {Kseniya Vasil'evna Belyaeva and Lina Pavlovna Nikitina and Anastasiya Grigor'evna Mal'kina and Andrei Valer'evich Afonin and Boris Aleksandrovich Trofimov},
title = {Cyanoacetylene-driven base catalyzed synthesis of dihydropyrimidophenanthridinones from phenanthridine and water},
journal = {Mendeleev Communications},
year = {2019},
volume = {30},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.004},
number = {1},
pages = {12--14},
doi = {10.1016/j.mencom.2020.01.004}
}
MLA
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Belyaeva, Kseniya Vasil'evna, et al. “Cyanoacetylene-driven base catalyzed synthesis of dihydropyrimidophenanthridinones from phenanthridine and water.” Mendeleev Communications, vol. 30, no. 1, Dec. 2019, pp. 12-14. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.01.004.

Keywords

alkynes
Annulation
nucleophilic addition
phenanthridine
zwitterions

Abstract

3-Arylpropynenitriles are readily annulated with phenanthridine in the KOH/H2O/MeCN system at room temperature to afford 4-aryl-1,13b dihydropyrimido[1,2-f]phenanthridin-2-ones. The moderate yield of the products can be rationalized by the anionic oligomerization of an intermediate zwitterion adduct of the reactants. The reaction represents a single-stage access to a new family of pharmaceutically prospective compounds.

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