The behavior of 2-chloroquinoline-3-carbaldehyde and 2-oxoquinoline-3-carbaldehyde toward stabilized methylenetriphenylphosphoranes and secondary amines

Abstract

<p>In this study use was made of the Wittig carbonyl olefination reaction and stereo-identification of the resulting alkenes. Condensation of 2-chloroquinoline-3-carbaldehyde with some selected stabilized phosphonium ylides yielded a mixture of the corresponding E and Z olefins in each case. On the other hand reaction of 2-oxoquinoline-3-carbaldehyde with the selected ylides afforded the respective olefins only in one of the possible stereoisomers. The reaction of 2-chloroquinoline-3-carbaldehyde with acetylmethylenetriphenylphosphorane produced the respective olefine together with acridin-3-ol. Heating of (E) and/or (Z)-methyl 3-(2-chloroquinolin-3-yl)acrylate with hydrazine hydrate yielded the corresponding propan-1-ol derivative. Dechlorination of (E)-ethyl 3-(2-chloroquinolin-3-yl)acrylate and/or (E)-4-(2-chloroquinolin-3-yl)but-3-en-2-one was effected upon treatment with morpholine or piperidine in absolute ethanol to give the respective enone derivatives.</p