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Different Behavior of 2-Substituted 3-Nitro-2H-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters. / Kochnev, Ivan A.; Barkov, Alexey Y.; Simonov, Nikita S. et al.
In: Molecules, Vol. 27, No. 24, 8983, 16.12.2022.

Research output: Contribution to journal › Article › peer-review

Harvard

Kochnev, IA, Barkov, AY, Simonov, NS, Ulitko, MV, Zimnitskiy, NS, Korotaev, VY & Sosnovskikh, VY 2022, 'Different Behavior of 2-Substituted 3-Nitro-2H-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters', Molecules, vol. 27, no. 24, 8983. https://doi.org/10.3390/molecules27248983

APA

Kochnev, I. A., Barkov, A. Y., Simonov, N. S., Ulitko, M. V., Zimnitskiy, N. S., Korotaev, V. Y., & Sosnovskikh, V. Y. (2022). Different Behavior of 2-Substituted 3-Nitro-2H-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters. Molecules, 27(24), [8983]. https://doi.org/10.3390/molecules27248983

Vancouver

Kochnev IA, Barkov AY, Simonov NS, Ulitko MV, Zimnitskiy NS, Korotaev VY et al. Different Behavior of 2-Substituted 3-Nitro-2H-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters. Molecules. 2022 Dec 16;27(24):8983. doi: 10.3390/molecules27248983

Author

Kochnev, Ivan A. ; Barkov, Alexey Y. ; Simonov, Nikita S. et al. / Different Behavior of 2-Substituted 3-Nitro-2H-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters. In: Molecules. 2022 ; Vol. 27, No. 24.

BibTeX

@article{86fac3135f534320b216d3bac781762f,
title = "Different Behavior of 2-Substituted 3-Nitro-2H-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters",
abstract = "The AgOAc-catalysed reaction of 3-nitro-2-phenyl-2H-chromenes with stabilized azomethine ylides generated from the imines based on methyl glycinate and arylaldehydes leads to a mixture of endo and endo{\textquoteright} isomers of the corresponding chromeno[3,4-c]pyrrolidines in a ratio of 2.0–2.3:1 in 85–93% total yields as a result of a Michael addition/Mannich reaction sequence. In a similar reaction involving 2-trifluoromethyl-3-nitro-2H-chromenes, only endo chromeno[3,4-c]pyrrolidines are formed in 85–94% yields. 3-Nitro-2-(trichloromethyl)-2H-chromenes under the same conditions react with these azomethine ylides to give the corresponding Michael adducts as individual anti-isomers with the cis,trans-configuration of the chromane ring in 40–67% yields. Some 4-CF3-substituted chromano[3,4-c]pyrrolidines exhibited high cytotoxic activity against HeLa human cervical carcinoma cells.",
author = "Kochnev, {Ivan A.} and Barkov, {Alexey Y.} and Simonov, {Nikita S.} and Ulitko, {Maria V.} and Zimnitskiy, {Nikolay S.} and Korotaev, {Vladislav Y.} and Sosnovskikh, {Vyacheslav Y.}",
year = "2022",
month = dec,
day = "16",
doi = "10.3390/molecules27248983",
language = "English",
volume = "27",
journal = "Molecules",
issn = "1420-3049",
publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",
number = "24",

}

RIS

TY - JOUR

T1 - Different Behavior of 2-Substituted 3-Nitro-2H-chromenes in the Reaction with Stabilized Azomethine Ylides Generated from α-Iminoesters

AU - Kochnev, Ivan A.

AU - Barkov, Alexey Y.

AU - Simonov, Nikita S.

AU - Ulitko, Maria V.

AU - Zimnitskiy, Nikolay S.

AU - Korotaev, Vladislav Y.

AU - Sosnovskikh, Vyacheslav Y.

PY - 2022/12/16

Y1 - 2022/12/16

N2 - The AgOAc-catalysed reaction of 3-nitro-2-phenyl-2H-chromenes with stabilized azomethine ylides generated from the imines based on methyl glycinate and arylaldehydes leads to a mixture of endo and endo’ isomers of the corresponding chromeno[3,4-c]pyrrolidines in a ratio of 2.0–2.3:1 in 85–93% total yields as a result of a Michael addition/Mannich reaction sequence. In a similar reaction involving 2-trifluoromethyl-3-nitro-2H-chromenes, only endo chromeno[3,4-c]pyrrolidines are formed in 85–94% yields. 3-Nitro-2-(trichloromethyl)-2H-chromenes under the same conditions react with these azomethine ylides to give the corresponding Michael adducts as individual anti-isomers with the cis,trans-configuration of the chromane ring in 40–67% yields. Some 4-CF3-substituted chromano[3,4-c]pyrrolidines exhibited high cytotoxic activity against HeLa human cervical carcinoma cells.

AB - The AgOAc-catalysed reaction of 3-nitro-2-phenyl-2H-chromenes with stabilized azomethine ylides generated from the imines based on methyl glycinate and arylaldehydes leads to a mixture of endo and endo’ isomers of the corresponding chromeno[3,4-c]pyrrolidines in a ratio of 2.0–2.3:1 in 85–93% total yields as a result of a Michael addition/Mannich reaction sequence. In a similar reaction involving 2-trifluoromethyl-3-nitro-2H-chromenes, only endo chromeno[3,4-c]pyrrolidines are formed in 85–94% yields. 3-Nitro-2-(trichloromethyl)-2H-chromenes under the same conditions react with these azomethine ylides to give the corresponding Michael adducts as individual anti-isomers with the cis,trans-configuration of the chromane ring in 40–67% yields. Some 4-CF3-substituted chromano[3,4-c]pyrrolidines exhibited high cytotoxic activity against HeLa human cervical carcinoma cells.

UR - http://www.scopus.com/inward/record.url?partnerID=8YFLogxK&scp=85144511486

UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=000904212300001

U2 - 10.3390/molecules27248983

DO - 10.3390/molecules27248983

M3 - Article

C2 - 36558115

VL - 27

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 24

M1 - 8983

ER -

ID: 33191636