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Stereoselective Synthesis of Multisubstituted Cyclohexanes by Reaction of Conjugated Enynones with Malononitrile in the Presence of LDA. / Igushkina, Anastasiya V.; Golovanov, Alexander A.; Boyarskaya, Irina A.; Kolesnikov, Ilya E.; Vasilyev, Aleksander V.

в: Molecules (Basel, Switzerland), Том 25, № 24, 14.12.2020.

Результаты исследований: Научные публикации в периодических изданияхстатьяРецензирование

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@article{059ba670488345ac9a433319364090ce,
title = "Stereoselective Synthesis of Multisubstituted Cyclohexanes by Reaction of Conjugated Enynones with Malononitrile in the Presence of LDA",
abstract = "Reaction of linear conjugated enynones, 1,5-diarylpent-2-en-4-yn-1-ones, with malononitrile in the presence of lithium diisopropylamide LDA, as a base, in THF at room temperature for 3-7 h resulted in the formation of the product of dimerization, multisubstituted polyfunctional cyclohexanes, 4-aryl-2,6-bis(arylethynyl)-3-(aryloxomethyl)-4-hydroxycyclohexane-1,1-dicarbonitriles, in yields up to 60%. Varying the reaction conditions by decreasing time and temperature and changing the ratio of starting compounds (enynone and malononitrile) allowed isolating some intermediate compounds, which confirmed a plausible reaction mechanism. The relative stability of possible stereoisomers of such cyclohexanes was estimated by quantum chemical calculations (DFT method). The obtained cyclohexanes were found to possess photoluminescent properties.",
keywords = "carbanionic reactions, conjugated enynones, cyclohexanes, malononitrile, photoluminescent compounds",
author = "Igushkina, {Anastasiya V.} and Golovanov, {Alexander A.} and Boyarskaya, {Irina A.} and Kolesnikov, {Ilya E.} and Vasilyev, {Aleksander V.}",
note = "Copyright: This record is sourced from MEDLINE/PubMed, a database of the U.S. National Library of Medicine",
year = "2020",
month = dec,
day = "14",
doi = "10.3390/molecules25245920",
language = "English",
volume = "25",
journal = "Molecules",
issn = "1420-3049",
publisher = "MDPI AG",
number = "24",

}

RIS

TY - JOUR

T1 - Stereoselective Synthesis of Multisubstituted Cyclohexanes by Reaction of Conjugated Enynones with Malononitrile in the Presence of LDA

AU - Igushkina, Anastasiya V.

AU - Golovanov, Alexander A.

AU - Boyarskaya, Irina A.

AU - Kolesnikov, Ilya E.

AU - Vasilyev, Aleksander V.

N1 - Copyright: This record is sourced from MEDLINE/PubMed, a database of the U.S. National Library of Medicine

PY - 2020/12/14

Y1 - 2020/12/14

N2 - Reaction of linear conjugated enynones, 1,5-diarylpent-2-en-4-yn-1-ones, with malononitrile in the presence of lithium diisopropylamide LDA, as a base, in THF at room temperature for 3-7 h resulted in the formation of the product of dimerization, multisubstituted polyfunctional cyclohexanes, 4-aryl-2,6-bis(arylethynyl)-3-(aryloxomethyl)-4-hydroxycyclohexane-1,1-dicarbonitriles, in yields up to 60%. Varying the reaction conditions by decreasing time and temperature and changing the ratio of starting compounds (enynone and malononitrile) allowed isolating some intermediate compounds, which confirmed a plausible reaction mechanism. The relative stability of possible stereoisomers of such cyclohexanes was estimated by quantum chemical calculations (DFT method). The obtained cyclohexanes were found to possess photoluminescent properties.

AB - Reaction of linear conjugated enynones, 1,5-diarylpent-2-en-4-yn-1-ones, with malononitrile in the presence of lithium diisopropylamide LDA, as a base, in THF at room temperature for 3-7 h resulted in the formation of the product of dimerization, multisubstituted polyfunctional cyclohexanes, 4-aryl-2,6-bis(arylethynyl)-3-(aryloxomethyl)-4-hydroxycyclohexane-1,1-dicarbonitriles, in yields up to 60%. Varying the reaction conditions by decreasing time and temperature and changing the ratio of starting compounds (enynone and malononitrile) allowed isolating some intermediate compounds, which confirmed a plausible reaction mechanism. The relative stability of possible stereoisomers of such cyclohexanes was estimated by quantum chemical calculations (DFT method). The obtained cyclohexanes were found to possess photoluminescent properties.

KW - carbanionic reactions

KW - conjugated enynones

KW - cyclohexanes

KW - malononitrile

KW - photoluminescent compounds

UR - http://www.scopus.com/inward/record.url?scp=85098607716&partnerID=8YFLogxK

U2 - 10.3390/molecules25245920

DO - 10.3390/molecules25245920

M3 - Article

C2 - 33327655

AN - SCOPUS:85098607716

VL - 25

JO - Molecules

JF - Molecules

SN - 1420-3049

IS - 24

ER -

ID: 72834456