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An unusual acetylene–allene rearrangement in iodomethylates of cotarnine acetylene derivatives

Lev Yur'evich Ukhin 1
Lev Yur'evich Ukhin
, 
Ludmila G Kuz'mina 2
Ludmila G Kuz'mina
, 
Tatyana N Gribanova 1
Tatyana N Gribanova
, 
Lyudmila Viktorovna Belousova 1
Lyudmila Viktorovna Belousova
, 
Evgenii Nikolaevich Shepelenko 3
Evgenii Nikolaevich Shepelenko
, 
Gennadii Sergeevich Borodkin 1
Gennadii Sergeevich Borodkin
,  , 
Vitaly Alekseevich Podshibyakin 1
Vitaly Alekseevich Podshibyakin
, 
Natalia Victorovna Stankevich 1
Natalia Victorovna Stankevich
10.1016/j.mencom.2021.03.036
Published 2021-03-03
Communication , Volume 31, Issue 2, 251-253
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Ukhin L. Y. et al. An unusual acetylene–allene rearrangement in iodomethylates of cotarnine acetylene derivatives // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 251-253.
GOST all authors (up to 50) Copy
Ukhin L. Y., Kuz'mina L. G., Gribanova T. N., Belousova L. V., Shepelenko E. N., Borodkin G. S., Dmitrieva O. I., Podshibyakin V. A., Stankevich N. V. An unusual acetylene–allene rearrangement in iodomethylates of cotarnine acetylene derivatives // Mendeleev Communications. 2021. Vol. 31. No. 2. pp. 251-253.
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TY - JOUR
DO - 10.1016/j.mencom.2021.03.036
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.036
TI - An unusual acetylene–allene rearrangement in iodomethylates of cotarnine acetylene derivatives
T2 - Mendeleev Communications
AU - Ukhin, Lev Yur'evich
AU - Kuz'mina, Ludmila G
AU - Gribanova, Tatyana N
AU - Belousova, Lyudmila Viktorovna
AU - Shepelenko, Evgenii Nikolaevich
AU - Borodkin, Gennadii Sergeevich
AU - Dmitrieva, Olga Igorevna
AU - Podshibyakin, Vitaly Alekseevich
AU - Stankevich, Natalia Victorovna
PY - 2021
DA - 2021/03/03
PB - Mendeleev Communications
SP - 251-253
IS - 2
VL - 31
ER -
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@article{2021_Ukhin,
author = {Lev Yur'evich Ukhin and Ludmila G Kuz'mina and Tatyana N Gribanova and Lyudmila Viktorovna Belousova and Evgenii Nikolaevich Shepelenko and Gennadii Sergeevich Borodkin and Olga Igorevna Dmitrieva and Vitaly Alekseevich Podshibyakin and Natalia Victorovna Stankevich},
title = {An unusual acetylene–allene rearrangement in iodomethylates of cotarnine acetylene derivatives},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.036},
number = {2},
pages = {251--253},
doi = {10.1016/j.mencom.2021.03.036}
}
MLA
Cite this
MLA Copy
Ukhin, Lev Yur'evich, et al. “An unusual acetylene–allene rearrangement in iodomethylates of cotarnine acetylene derivatives.” Mendeleev Communications, vol. 31, no. 2, Mar. 2021, pp. 251-253. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.03.036.

Keywords

acetylene–allene rearrangement
cotarnine acetylene derivatives
iodomethylation
isoquinolinium compounds
quantum-chemical calculations
X-ray

Abstract

N-Methylation of cotarnine–phenol propargyl ethers conjugates with MeI affords the corresponding quaternary ammonium derivatives with retained acetylenic moiety. 3-Hydroxyalk-1-yn-1-yl analogues in the course of such iodomethylation undergo isomerization into allenic derivatives which are transformed into acetylenic ones upon dissolution in DMSO.

References

1.
10.1016/j.mencom.2021.03.036_bib0005
Mashkovsky
Lekarstvennye sredstva (Medicines), 2005
2.
A New Total Synthesis of (±)-α-Noscapine
Zhao D., Mao Y., Song S., Cheng M.
Heterocycles, 2013
3.
One-pot synthesis of 4-heteroaryl-1,2-dihydro-3-benzazepines from 3,4-dihydroisoquinolinium salts or pseudo bases
Zubenko A.A., Kartsev V.G., Morkovnik A.S., Divaeva L.N., Alexeenko D.V., Suponitsky K.Y., Borodkin G.S., Klimenko A.I.
Tetrahedron Letters, 2017
4.
10.1016/j.mencom.2021.03.036_bib0020
Anh
Acta Crystallogr., 2017
6.
Synthesis and Antiproliferative Activity of 9‐Formyl and 9‐Ethynyl Noscapines
Reddy Nagireddy P.K., Kommalapati V.K., Manchukonda N.K., Sridhar B., Tangutur A.D., Kantevari S.
ChemistrySelect, 2019
7.
New Structural Modifications of Cotarnine Alkaloid Derivatives: Cotarnone and Dihydrocotarnine
Kartsev V.G., Zubenko A.A., Divaeva L.N., Morkovnik A.S., Baryshnikova T.K., Shirinian V.Z.
Russian Journal of General Chemistry, 2020
8.
L. Yu. Ukhin, K. Yu. Suponitskii and V. G. Kartsev, in Abstracts of the First International Conference ‘Chemistry and Biological Activity of Nitrogen Heterocycles and Alkaloids’, Moscow, 2001, vol. 1, p. 552.
9.
Alkynylation of Cotarnine Hydrochloride by Ag(I) Acetylenides
Ukhin L.Y., Suponitskii K.Y., Kartsev V.G.
Chemistry of Natural Compounds, 2003
10.
Alkynation of Chlorinated Cotarnine by Silver Propargylamines
Ukhin L.Y., Gol'ding I.R., Kartsev V.G.
Chemistry of Natural Compounds, 2004
11.
One-pot synthesis of cotarnine 1-alkynyl derivatives
Ukhin L.Y., Shepelenko E.N., Belousova L.V., Popova O.S., Alekseenko D.V.
Russian Chemical Bulletin, 2016
12.
10.1016/j.mencom.2021.03.036_bib0060
Temnikova
Molekulyarnye peregruppirovki v organicheskoi khimii (Molecular Rearrangements in Organic Chemistry), 1983
13.
Unsaturated and carbocyclic nucleoside analogues: synthesis, antitumor, and antiviral activity.
Phadtare S., Kessel D., Corbett T.H., Renis H.E., Court B.E., Zemlicka J.
Journal of Medicinal Chemistry, 1991
16.
10.1016/j.mencom.2021.03.036_sbref0080a
Smith
March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 2007
17.
10.1016/j.mencom.2021.03.036_sbref0080b
Smith
March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 2007
18.
10.1016/j.mencom.2021.03.036_sbref0080c
Smith
March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 2007
19.
Progress in the chemistry of nitrogen-, oxygen- And sulfur-containing heterocyclic systems
Danilkina N.A., Vasileva A.A., Balova I.A.
Russian Chemical Reviews, 2020