Studies on Ketene and its Derivatives. III

1 January 1963

journal article
Published by Pharmaceutical Society of Japan in YAKUGAKU ZASSHI

Vol. 83 (3) , 267-271
https://doi.org/10.1248/yakushi1947.83.3_267

Abstract

Reaction of quinoline with diketene afforded C₁₇H₁₃O₃N (II) which was transformed into dehydro-derivative C₁₇H₁₁O₃N (III) and dihydro-derivative C₁₇H₁₅O₃N (IV) by a disproportionating reaction. Hydrolysis of III with potassium hydroxide gave C₁₇H₁₃O₄N (VII) and C₁₅H₁₁O₃N (VIII). III was reobtained by treatment of VII with conc. hydrochloric acid. Reaction of III with liquid ammonia afforded C₁₇H₁₂O₂N₂ (V). The above reactions can be explained by suggesting the formula (IIa or IIb) for II which is in accordance with a structure proposed by Berson to a Wollenberg-compound prepared from pyridine and ketene.

Keywords

KETONES
QUINOLINES

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