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

Anastasiya V Igushkina, Alexander A Golovanov, Irina A Boyarskaya, Ilya E Kolesnikov, Aleksander V Vasilyev

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Article in Molecules (Basel, Switzerland), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it

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2citing papers in PubMed

0.6field-weighted citation impact, top 30% of its field

1 · What the graph read from it

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3 · Its place in the literature

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2 citing papers in PubMed, 11 citations in OpenAlex.

Synthesis, Reactions, and Agrochemical Studies of New 4,6-Diaryl-2-hydrazinylnicotinonitriles.International journal of molecular sciences · 2025
Article
Michael Addition of 3-Oxo-3-phenylpropanenitrile to Linear Conjugated Enynones: Approach to Polyfunctional δ-Diketones as Precursors for Heterocycle Synthesis.Molecules (Basel, Switzerland) · 2022
Article

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5 · Who and what money

Authors and funding

5 authors at 2 institutions in 1 country.

Anastasiya V IgushkinaDepartment of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, 199034 Saint Petersburg, Russia.

Alexander A GolovanovDepartment of Chemistry, Chemical Processes and Technologies, Togliatti State University, Belorusskaya ul., 14, 445667 Togliatti, Russia.

Irina A BoyarskayaDepartment of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, 199034 Saint Petersburg, Russia.

Ilya E KolesnikovCenter for Optical and Laser Materials Research, St. Petersburg State University, Ulyanovskaya ul., 5, 198504 Saint Petersburg, Russia.

Aleksander V VasilyevDepartment of Organic Chemistry, Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, 199034 Saint Petersburg, Russia.ORCID 0000-0003-3628-1492

St Petersburg University · RUTogliatti State University · RU

Funding

Russian Scientific Foundationm 18-13-00008

6 · The paper itself

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.

Indexed as

AlkenesCatalysisChemistry Techniques, SyntheticCyclohexanesDimerizationHumansLuminescent MeasurementsMolecular StructureNitrilesPropylaminesQuantum TheoryStereoisomerismTemperatureAlkenesCyclohexanesdicyanmethanediisopropylamineNitrilesPropylaminescarbanionic reactionsconjugated enynonescyclohexanesmalononitrilephotoluminescent compounds

Identifiers

PMID33327655

DOI10.3390/molecules25245920

PMCPMC7765106

OpenAlexW3111010205

What OpenQuestion holds

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LicenceCC BY

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Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.