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Generation and cascade reactions of N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium species

Konstantin Pavlovich Trainov 1
Konstantin Pavlovich Trainov
, 
Rinat Faritovich Salikov 1
Rinat Faritovich Salikov
, 
Alexander Yuryevich Belyy 1
Alexander Yuryevich Belyy
, 
Agata Nikolaevna Kuznetsova 1, 2
Agata Nikolaevna Kuznetsova
, 
Mikhail Dmitrievich Khitrov 1, 2
Mikhail Dmitrievich Khitrov
, 
Matvey Kirillovich Ilyushchenko 1, 2
Matvey Kirillovich Ilyushchenko
, 
Alena D Sokolova 1
Alena D Sokolova
, 
Dmitry Nikolaevich Platonov 1
Dmitry Nikolaevich Platonov
, 
10.1016/j.mencom.2022.03.037
Published 2022-03-06
Communication , Volume 32, Issue 2, 262-264
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Trainov K. P. et al. Generation and cascade reactions of N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium species // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 262-264.
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Trainov K. P., Salikov R. F., Belyy A. Y., Kuznetsova A. N., Khitrov M. D., Ilyushchenko M. K., Sokolova A. D., Platonov D. N., Tomilov Y. V. Generation and cascade reactions of N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium species // Mendeleev Communications. 2022. Vol. 32. No. 2. pp. 262-264.
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TY - JOUR
DO - 10.1016/j.mencom.2022.03.037
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.037
TI - Generation and cascade reactions of N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium species
T2 - Mendeleev Communications
AU - Trainov, Konstantin Pavlovich
AU - Salikov, Rinat Faritovich
AU - Belyy, Alexander Yuryevich
AU - Kuznetsova, Agata Nikolaevna
AU - Khitrov, Mikhail Dmitrievich
AU - Ilyushchenko, Matvey Kirillovich
AU - Sokolova, Alena D
AU - Platonov, Dmitry Nikolaevich
AU - Tomilov, Yury Vasil'evich
PY - 2022
DA - 2022/03/06
PB - Mendeleev Communications
SP - 262-264
IS - 2
VL - 32
ER -
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@article{2022_Trainov,
author = {Konstantin Pavlovich Trainov and Rinat Faritovich Salikov and Alexander Yuryevich Belyy and Agata Nikolaevna Kuznetsova and Mikhail Dmitrievich Khitrov and Matvey Kirillovich Ilyushchenko and Alena D Sokolova and Dmitry Nikolaevich Platonov and Yury Vasil'evich Tomilov},
title = {Generation and cascade reactions of N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium species},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.037},
number = {2},
pages = {262--264},
doi = {10.1016/j.mencom.2022.03.037}
}
MLA
Cite this
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Trainov, Konstantin Pavlovich, et al. “Generation and cascade reactions of N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium species.” Mendeleev Communications, vol. 32, no. 2, Mar. 2022, pp. 262-264. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.03.037.

Keywords

N-vinylpyridinium salts
acetylenedicarboxylates
cascade reactions
cycloheptatrieneheptacarboxylates
diastereomers

Abstract

The configuration of N-[1,2-bis(methoxycarbonyl)vinyl]-pyridinium intermediate generated from stereoisomers of dimethyl dibromosuccinate or dimethyl bromobutenedioate does not depend on the precursors’ configuration, as distinct from the yields and the reaction rates. The use of various nucleophiles in these cascade reactions gives either cycloheptadieneoctacarboxylic or cycloheptatrienehepta-carboxylic esters along with pyridinium 5-dicyano-methylidene-2,3,4-tris(methoxycarbonyl)cyclopenta-1,3-dien-1-olate. In the latter case, the acyclic ‘Diels’ golden adduct’ was detected, and its structure was refined.

References

1.
Pentacarboxycyclopentadienes in Organic Synthesis
Mikhailov I.E., Dushenko G.A., Minkin V.I.
Russian Journal of Organic Chemistry, 2021
2.
Organocatalytic cascade reactions as a new tool in total synthesis.
Grondal C., Jeanty M., Enders D.
Nature Chemistry, 2010
4.
Tukhtaev H.B., Sorokin I.D., Melnikov M.Y., Budynina E.M.
Mendeleev Communications, 2020
5.
Schmidt E.Y., Semenova N.V., Ivanova E.V., Bidusenko I.A., Trofimov B.A.
Mendeleev Communications, 2020
6.
Zyryanov G.V., Kopchuk D.S., Kovalev I.S., Santra S., Rahman M., Khasanov A.F., Krinochkin A.P., Taniya O.S., Chupakhin O.N., Charushin V.N.
Mendeleev Communications, 2020
7.
Elinson M.N., Vereshchagin A.N., Anisina Y.E., Leonova N.A., Egorov M.P.
Mendeleev Communications, 2020
8.
Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis
Stephanidou-Stephanatou J., Neochoritis C., Zarganes-Tzitzikas T.
Synthesis, 2014
11.
A Novel Three Component Reaction: The Synthesis of Stable, Highly Functionalized 1,4-Diionic Nitrogen Betaines
Shaabani A., Soleimani E.
Phosphorus, Sulfur and Silicon and the Related Elements, 2006
13.
A Simple Synthesis of Stable 1,4-Diionic Pyridinium Betaines
Yavari I., Anary-Abbasinejad M., Alizadeh A.
Monatshefte fur Chemie, 2002
18.
Synthesis of 1,2,3,4,5-Penta(methoxycarbonyl)cyclopentadienides through Electrocyclic Ring Closure and Ring Contraction Reactions
Salikov R.F., Trainov K.P., Platonov D.N., Belyy A.Y., Tomilov Y.V.
European Journal of Organic Chemistry, 2018
22.
Synthesis and activity studies of analogues of the rat selective toxicant norbormide.
Rennison D., Bova S., Cavalli M., Ricchelli F., Zulian A., Hopkins B., Brimble M.A.
Bioorganic and Medicinal Chemistry, 2007
23.
A mild and selective dehydrohalogenating agent
Kendall J.T., Lemal D.M.
Journal of Fluorine Chemistry, 1997
24.
Reactivity of fluorine in fluorinated succinic esters
Hudlicky M.
Journal of Fluorine Chemistry, 1972
25.
Synthesis and TD-DFT investigation of arylhydrazonocyclopentadiene dyes
Salikov R.F., Trainov K.P., Platonov D.N., Davydov D.A., Lee S., Gerasimov I.S., Medvedev M.G., Levina A.A., Belyy A.Y., Tomilov Y.V.
Dyes and Pigments, 2019
26.
Electron deficient 5-hydroxy-1,2-dihydroisoquinolin-1-ones – A new class of fluorescent dyes with large Stokes shifts
Belyy A.Y., Platonov D.N., Salikov R.F., Trainov K.P., Medvedev M.G., Luponosov Y.N., Svidchenko E.A., Tomilov Y.V.
Dyes and Pigments, 2021
27.
10.1016/j.mencom.2022.03.037_b0135
Cookson
J. Chem. Soc., C, 1986
28.
10.1016/j.mencom.2022.03.037_b0140
Erickson
J. Am. Chem. Soc., 1867