Hiroshi Noda

Photochemical reactions of β-aminovinyl phenyl ketones and related compounds

Photochemical reactions of some β-aminovinyl ketones and related compounds have been examined. Irradiation of the β-NN-dialkylaminovinyl phenyl ketones (1a–g) yielded the corresponding pyrroles (2a–g′), while ketones (1h–m) were inert. Irradiation of the (β-benzoylvinyl)trialkylammonium chlorides (7a and b) afforded the 1,4-diketones (8a and b) respectively. Irradiation of β-ethoxyvinyl phenyl ketone (5) gave an intractable mixture, while the corresponding thioketone (6) was photochemically inactive. Photolysis of the 2-dialkylaminobenzophenones (9a and b) gave the corresponding indoles (10a and b) respectively, accompanied by dealkylation products. The formation of the pyrrole was presumed to occur from the n–π* triplet state. The mechanisms of these photochemical reactions are discussed.

Studies on tertiary amine oxides—LII: Reaction of 4-nitroquinoline 1-oxide with enamines of isobutyraldehyde. A novel cyclization reaction involving participation of the nitro group☆

Abstract When a chloroform solution of 4-nitroquinoline 1-oxide ( 1 ) and 2 equivalents of an enamine of isobutyraldehyde ( 4 ) is kept at room temp for a prolonged time, a novel cyclization reaction occurs to produce 1-hydroxy-2-oxo-3,3-dimethylpyrrolido[4,5-c]quinoline 5-oxide ( 5 ) or/and the corresponding 1-deoxy compound ( 6 ). Their structures were established by spectral and chemical examinations. The reaction mechanisms are also discussed.

REACTION OF PICOLINE AND METHYLQUINOLINE N-OXIDES, WITH THALLIUM TRIACETATE

Das N-Oxid (I) reagiert mit Thallium(III)-acetat und Essigsaureanhydrid, Essigsaure bei Raumtemperatur zum Acetoxymethylderivat (II).