Reaction of 2-methylquinoline with 3-phenylprop-2-ynenitrile in the KOH—H2O system View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

2017-12

AUTHORS

K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, A. V. Vashchenko, B. A. Trofimov

ABSTRACT

The reaction of 2-methylquinoline with 3-phenylprop-2-ynenitrile in the presence of water (0—25 °C, 20 mol.% KOH, 5 equiv. H2O) is accompanied by the loss of aromaticity of the quinoline nucleus and results in double functionalization of the molecule at the nitrogen atom and the methyl group. Two 2-cyano-1-phenylethenyl groups were introduced into the molecule to form (2E,4E)-4-{1-[(Z)-2-cyano-1-phenylethenyl]quinolin-2(1H)-ylidene}-3-phenylbut-2-enenitrile in 59—67% yield. This reaction is stereoselective: the N-2-cyano-1-phenylethenyl-substituent has the Z-configuration, while the 1,3-diene moiety at the methyl group has the E,E-configuration. (2E)-3-Phenyl-4-(quinolin-2-yl)but-2-enenitrile that formed as a by-product (0—24% yields) is formally the addition product of the methyl group of the quinoline substrate at the acetylenic bond. More... »

PAGES

2258-2263

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-017-2011-5

DOI

http://dx.doi.org/10.1007/s11172-017-2011-5

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https://app.dimensions.ai/details/publication/pub.1101539614


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