Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines
Vladimir A Motornov
1, 2, 3, 4, 5, 6, 7
,
Andrey A Tabolin
1, 3, 4, 5, 6
,
Yulia V. Nelyubina
4, 5, 6, 8, 9
,
Valentine G. Nenajdenko
6, 10, 11, 12, 13
,
Sema L. Ioffe
1, 3, 4, 5, 6
4
RUSSIAN ACADEMY OF SCIENCES
5
Moscow
6
Russia
|
7
Higher Chemical College
11
DEPARTMENT OF CHEMISTRY
13
Moscow 119991
Publication type: Journal Article
Publication date: 2019-01-16
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
30672946
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A general method for the synthesis of substituted indolizines by copper(II) acetate-promoted oxidative [3 + 2]-annulation of α-fluoronitroalkenes with in situ generated pyridinium ylides was developed. Application of the copper(II) acetate–2,6-lutidine system provides efficient access to various 1-fluoroindolizines in up to 81% yield. Both electron-rich and electron-deficient nitroalkenes as well as different pyridinium and isoquinolinium salts can be involved in the reaction. Moreover, it was found that copper-mediated annulation is applicable for other α-substituted (alkyl, chloro, and ester) nitroalkenes giving rise to the corresponding indolizines. First synthesis of monofluorinated [3,2,2]cyclazines was demonstrated via oxidative annulation of 3-unsubstituted fluoroindolizines with diethyl acetylene dicarboxylate.
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Total citations:
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Citations from 2024:
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(21.16%)
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Motornov V. A. et al. Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines // Organic and Biomolecular Chemistry. 2019. Vol. 17. No. 6. pp. 1442-1454.
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Motornov V. A., Tabolin A. A., Nelyubina Y. V., Nenajdenko V. G., Ioffe S. L. Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines // Organic and Biomolecular Chemistry. 2019. Vol. 17. No. 6. pp. 1442-1454.
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RIS
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TY - JOUR
DO - 10.1039/C8OB03126F
UR - https://xlink.rsc.org/?DOI=C8OB03126F
TI - Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines
T2 - Organic and Biomolecular Chemistry
AU - Motornov, Vladimir A
AU - Tabolin, Andrey A
AU - Nelyubina, Yulia V.
AU - Nenajdenko, Valentine G.
AU - Ioffe, Sema L.
PY - 2019
DA - 2019/01/16
PB - Royal Society of Chemistry (RSC)
SP - 1442-1454
IS - 6
VL - 17
PMID - 30672946
SN - 1477-0520
SN - 1477-0539
ER -
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@article{2019_Motornov,
author = {Vladimir A Motornov and Andrey A Tabolin and Yulia V. Nelyubina and Valentine G. Nenajdenko and Sema L. Ioffe},
title = {Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines},
journal = {Organic and Biomolecular Chemistry},
year = {2019},
volume = {17},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://xlink.rsc.org/?DOI=C8OB03126F},
number = {6},
pages = {1442--1454},
doi = {10.1039/C8OB03126F}
}
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MLA
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Motornov, Vladimir A., et al. “Copper-mediated oxidative [3 + 2]-annulation of nitroalkenes and pyridinium ylides: general access to functionalized indolizines and efficient synthesis of 1-fluoroindolizines.” Organic and Biomolecular Chemistry, vol. 17, no. 6, Jan. 2019, pp. 1442-1454. https://xlink.rsc.org/?DOI=C8OB03126F.