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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.

In: Molecules (Basel, Switzerland), Vol. 25, No. 24, 14.12.2020.

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

Harvard

Igushkina, AV, Golovanov, AA, Boyarskaya, IA, Kolesnikov, IE & Vasilyev, AV 2020, 'Stereoselective Synthesis of Multisubstituted Cyclohexanes by Reaction of Conjugated Enynones with Malononitrile in the Presence of LDA', Molecules (Basel, Switzerland), vol. 25, no. 24. https://doi.org/10.3390/molecules25245920

APA

Igushkina, A. V., Golovanov, A. A., Boyarskaya, I. A., Kolesnikov, I. E., & Vasilyev, A. V. (2020). Stereoselective Synthesis of Multisubstituted Cyclohexanes by Reaction of Conjugated Enynones with Malononitrile in the Presence of LDA. Molecules (Basel, Switzerland), 25(24). https://doi.org/10.3390/molecules25245920

Vancouver

Igushkina AV, Golovanov AA, Boyarskaya IA, Kolesnikov IE, Vasilyev AV. Stereoselective Synthesis of Multisubstituted Cyclohexanes by Reaction of Conjugated Enynones with Malononitrile in the Presence of LDA. Molecules (Basel, Switzerland). 2020 Dec 14;25(24). https://doi.org/10.3390/molecules25245920

Author

Igushkina, Anastasiya V. ; Golovanov, Alexander A. ; Boyarskaya, Irina A. ; Kolesnikov, Ilya E. ; Vasilyev, Aleksander V. / Stereoselective Synthesis of Multisubstituted Cyclohexanes by Reaction of Conjugated Enynones with Malononitrile in the Presence of LDA. In: Molecules (Basel, Switzerland). 2020 ; Vol. 25, No. 24.

BibTeX

@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