Home / Publications / A straightforward access to 2-hydroxyoxazino[3,2-f ]phenanthridines from phenanthridine, oxalylacetylenes and water

A straightforward access to 2-hydroxyoxazino[3,2-f ]phenanthridines from phenanthridine, oxalylacetylenes and water

, 
Lina Pavlovna Nikitina 1
Lina Pavlovna Nikitina
, 
Veronika Sergeevna Gen' 1
Veronika Sergeevna Gen'
, 
Anton Vasilievich Kuzmin 1
Anton Vasilievich Kuzmin
, 
Andrei Valer'evich Afonin 1
Andrei Valer'evich Afonin
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2022.07.004
Published 2022-07-01
Communication , Volume 32, Issue 4, 439-442
6
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Belyaeva K. V. et al. A straightforward access to 2-hydroxyoxazino[3,2-f ]phenanthridines from phenanthridine, oxalylacetylenes and water // Mendeleev Communications. 2022. Vol. 32. No. 4. pp. 439-442.
GOST all authors (up to 50) Copy
Belyaeva K. V., Nikitina L. P., Gen' V. S., Kuzmin A. V., Afonin A. V., Trofimov B. A. A straightforward access to 2-hydroxyoxazino[3,2-f ]phenanthridines from phenanthridine, oxalylacetylenes and water // Mendeleev Communications. 2022. Vol. 32. No. 4. pp. 439-442.
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TY - JOUR
DO - 10.1016/j.mencom.2022.07.004
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.004
TI - A straightforward access to 2-hydroxyoxazino[3,2-f ]phenanthridines from phenanthridine, oxalylacetylenes and water
T2 - Mendeleev Communications
AU - Belyaeva, Kseniya Vasil'evna
AU - Nikitina, Lina Pavlovna
AU - Gen', Veronika Sergeevna
AU - Kuzmin, Anton Vasilievich
AU - Afonin, Andrei Valer'evich
AU - Trofimov, Boris Aleksandrovich
PY - 2022
DA - 2022/07/01
PB - Mendeleev Communications
SP - 439-442
IS - 4
VL - 32
ER -
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@article{2022_Belyaeva,
author = {Kseniya Vasil'evna Belyaeva and Lina Pavlovna Nikitina and Veronika Sergeevna Gen' and Anton Vasilievich Kuzmin and Andrei Valer'evich Afonin and Boris Aleksandrovich Trofimov},
title = {A straightforward access to 2-hydroxyoxazino[3,2-f ]phenanthridines from phenanthridine, oxalylacetylenes and water},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.004},
number = {4},
pages = {439--442},
doi = {10.1016/j.mencom.2022.07.004}
}
MLA
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Belyaeva, Kseniya Vasil'evna, et al. “A straightforward access to 2-hydroxyoxazino[3,2-f ]phenanthridines from phenanthridine, oxalylacetylenes and water.” Mendeleev Communications, vol. 32, no. 4, Jul. 2022, pp. 439-442. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.07.004.

Keywords

13-dipolar intermediates
13-oxazines
alkynes
Annulation
diastereoselectivity
hemiacetals
phenanthridine
quantum chemical calculations

Abstract

Phenanthridine is readily annulated at room temperature with dihydro-1,3-oxazine ring under the action of oxalylacetylene ethyl ester to diastereoselectively deliver (R*,R*)-2-hydroxy-4-aryl-2H,13bH-[1,3]oxazino[3,2-f]- phenanthridines in up to 58% yield. According to quantum chemical calculations, among the possible transformations of the 1,3(4)-dipole phenanthridine/oxalylacetylene inter- mediate, protonated with water, the preferred route leading to the target product is attack of the hydroxyl anion at the carbonyl moiety, followed by closing of the oxazine ring. The calculated stability of oxazinophenanthridine with respect to the oxazinoquinoline derivative in terms of ΔG, and the higher C6–O bond order in the former are confirmed by experimental results of differences between the reactions of phenanthridine and quinoline with aryloxalylacetylenes in water.

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