Reaction of 2-methylquinoline with 3-phenylprop-2-ynenitrile in the KOH—H{sub 2}O system

Journal Article · Fri Dec 15 04:00:00 EST 2017 · Russian Chemical Bulletin

DOI:https://doi.org/10.1007/S11172-017-2011-5· OSTI ID:22863425

Belyaeva, K. V.; Nikitina, L. P.; Afonin, A. V.; Vashchenko, A. V.

The reaction of 2-methylquinoline with 3-phenylprop-2-ynenitrile in the presence of water (0—25 °C, 20 mol.% KOH, 5 equiv. H{sub 2}O) 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.

• OSTI ID: 22863425
• Journal Information: Russian Chemical Bulletin, Journal Name: Russian Chemical Bulletin Journal Issue: 12 Vol. 66; ISSN RCBUEY; ISSN 1066-5285
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
ACETYLENE
BY-PRODUCTS
CONFIGURATION
DIENES
MOLECULES
NITROGEN
POTASSIUM HYDROXIDES
QUINALDINE
SUBSTRATES
X-RAY DIFFRACTION
YIELDS
ZWITTERIONIC COMPOUNDS