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Stereoselective synthesis of novel functionalized cyclohexanone derivatives via the condensation of aromatic aldehydes with acetoacetamide and the influence of the ortho-effect and autocondensation. / Gein, Vladimir L.; Nosova, Natalia V.; Yankin, Andrei N.; Bazhina, Alina Y.; Dmitriev, Maksim V.

в: Tetrahedron Letters, Том 60, № 24, 13.06.2019, стр. 1592-1596.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

Harvard

Gein, VL, Nosova, NV, Yankin, AN, Bazhina, AY & Dmitriev, MV 2019, 'Stereoselective synthesis of novel functionalized cyclohexanone derivatives via the condensation of aromatic aldehydes with acetoacetamide and the influence of the ortho-effect and autocondensation', Tetrahedron Letters, Том. 60, № 24, стр. 1592-1596. https://doi.org/10.1016/j.tetlet.2019.05.023

APA

Gein, V. L., Nosova, N. V., Yankin, A. N., Bazhina, A. Y., & Dmitriev, M. V. (2019). Stereoselective synthesis of novel functionalized cyclohexanone derivatives via the condensation of aromatic aldehydes with acetoacetamide and the influence of the ortho-effect and autocondensation. Tetrahedron Letters, 60(24), 1592-1596. https://doi.org/10.1016/j.tetlet.2019.05.023

Vancouver

Gein VL, Nosova NV, Yankin AN, Bazhina AY, Dmitriev MV. Stereoselective synthesis of novel functionalized cyclohexanone derivatives via the condensation of aromatic aldehydes with acetoacetamide and the influence of the ortho-effect and autocondensation. Tetrahedron Letters. 2019 Июнь 13;60(24):1592-1596. https://doi.org/10.1016/j.tetlet.2019.05.023

Author

Gein, Vladimir L. ; Nosova, Natalia V. ; Yankin, Andrei N. ; Bazhina, Alina Y. ; Dmitriev, Maksim V. / Stereoselective synthesis of novel functionalized cyclohexanone derivatives via the condensation of aromatic aldehydes with acetoacetamide and the influence of the ortho-effect and autocondensation. в: Tetrahedron Letters. 2019 ; Том 60, № 24. стр. 1592-1596.

BibTeX

@article{d0a22adf7b444738982ec667447aa808,
title = "Stereoselective synthesis of novel functionalized cyclohexanone derivatives via the condensation of aromatic aldehydes with acetoacetamide and the influence of the ortho-effect and autocondensation",
abstract = " A simple, inexpensive and stereoselective synthesis of novel functionalized cyclohexanone derivatives via the reaction of acetoacetamide with aromatic aldehydes in ethanol at room temperature is described. Additionally, the presence of substituents such as –NO 2 and –Cl in the ortho-position of the aldehyde aromatic ring resulted in the formation of novel piperidines. The use of Lewis acids such as iron(III) chloride and bismuth(III) nitrate as catalysts led to autocondensation of acetoacetamide and the formation of 2,4-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide. ",
keywords = "Acetoacetamide, Autocondensation, Cyclohexanones, Heterocycles, ortho-Effect, Piperidines, GREENER APPROACH, ANTIBIOTICS, OPIOID DEPENDENCE, KETAMINE, DIASTEREOSELECTIVE SYNTHESIS, TETRACYCLINES, RELEASE NALTREXONE, EPOXYDON GROUP, REMIFENTANIL, ANTIMICROBIAL ACTIVITY",
author = "Gein, {Vladimir L.} and Nosova, {Natalia V.} and Yankin, {Andrei N.} and Bazhina, {Alina Y.} and Dmitriev, {Maksim V.}",
year = "2019",
month = jun,
day = "13",
doi = "10.1016/j.tetlet.2019.05.023",
language = "English",
volume = "60",
pages = "1592--1596",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier",
number = "24",

}

RIS

TY - JOUR

T1 - Stereoselective synthesis of novel functionalized cyclohexanone derivatives via the condensation of aromatic aldehydes with acetoacetamide and the influence of the ortho-effect and autocondensation

AU - Gein, Vladimir L.

AU - Nosova, Natalia V.

AU - Yankin, Andrei N.

AU - Bazhina, Alina Y.

AU - Dmitriev, Maksim V.

PY - 2019/6/13

Y1 - 2019/6/13

N2 - A simple, inexpensive and stereoselective synthesis of novel functionalized cyclohexanone derivatives via the reaction of acetoacetamide with aromatic aldehydes in ethanol at room temperature is described. Additionally, the presence of substituents such as –NO 2 and –Cl in the ortho-position of the aldehyde aromatic ring resulted in the formation of novel piperidines. The use of Lewis acids such as iron(III) chloride and bismuth(III) nitrate as catalysts led to autocondensation of acetoacetamide and the formation of 2,4-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide.

AB - A simple, inexpensive and stereoselective synthesis of novel functionalized cyclohexanone derivatives via the reaction of acetoacetamide with aromatic aldehydes in ethanol at room temperature is described. Additionally, the presence of substituents such as –NO 2 and –Cl in the ortho-position of the aldehyde aromatic ring resulted in the formation of novel piperidines. The use of Lewis acids such as iron(III) chloride and bismuth(III) nitrate as catalysts led to autocondensation of acetoacetamide and the formation of 2,4-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide.

KW - Acetoacetamide

KW - Autocondensation

KW - Cyclohexanones

KW - Heterocycles

KW - ortho-Effect

KW - Piperidines

KW - GREENER APPROACH

KW - ANTIBIOTICS

KW - OPIOID DEPENDENCE

KW - KETAMINE

KW - DIASTEREOSELECTIVE SYNTHESIS

KW - TETRACYCLINES

KW - RELEASE NALTREXONE

KW - EPOXYDON GROUP

KW - REMIFENTANIL

KW - ANTIMICROBIAL ACTIVITY

UR - http://www.scopus.com/inward/record.url?scp=85065901090&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2019.05.023

DO - 10.1016/j.tetlet.2019.05.023

M3 - Article

AN - SCOPUS:85065901090

VL - 60

SP - 1592

EP - 1596

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 24

ER -

ID: 42305688