690666-79-6Relevant academic research and scientific papers
An Efficient Synthesis of 2,4-Disubstituted Quinolines by Electrophile-Mediated Cyclization Reactions of 2-Isocyanostyrene Derivatives
Kobayashi, Kazuhiro,Takagoshi, Kenichi,Kondo, Shizuka,Morikawa, Osamu,Konishi, Hisatoshi
, p. 553 - 559 (2007/10/03)
A novel quinoline synthesis starting with 2-isocyanostyrene derivatives is described. The treatment of 2-isocyanostyrene derivatives with aldehydes (or acetone) in the presence of a catalytic amount of diethyl ether-boron trifluoride afforded quinoline derivatives carrying a 1-hydroxyalkyl substituent at the 2-position. The use of acetaldehyde diethyl acetal or phenyloxirane as an electrophile under the same conditions gave the corresponding quinoline derivatives, carrying the 1-ethoxyethyl or 2-hydroxy-2-phenylethyl substituent at the 2-position, respectively. 2-Isocyanostyrene derivatives reacted with N,N-dimethyliminium salts without any catalyst to give 2-(1-dimethylaminoalkyl)quinolines.
The formation of quinolin-2(1H)-ones via electrocyclic reaction of o-isocyanatostyrenes generated in situ from o-isocyanostyrenes
Kobayashi, Kazuhiro,Kitamura, Taichi,Yoneda, Keiichi,Morikawa, Osamu,Konishi, Hisatoshi
, p. 798 - 799 (2007/10/03)
A convenient one-pot preparation of 4-substituted or 3,4-disubstituted quinolin-2(1H)-ones from 2-isocyanostyrene derivatives, which involves mCPBA oxidation to the corresponding isocyanate intermediates followed by electrocyclization, is described.
