The corresponding 2-benzyl-3H-pyrido [3, 2, 1-kl] phenoxazin-3-ones (II-VI) were obtained by condensation of 1, 2-dihydro-3H-pyrido [3, 2, 1-kl] phenoxazin-3-one (1) with benzaldehyde, p-dimethylaminobenzaldehyde, p-chlorobenzaldehyde, p-methoxybenzaldehyde, and m-nitrobenzaldehyde, in ethanol containing sodium hydroxide. Reaction of I with semicarbazide, thiosemicarbazide, phenylsemicarbazide, and phenylthiosemicarbazide respectively gave the semicarbazone compounds (VII-X). Treatment of 3-hydrazono-1, 2-dihydro-3H-pyrido [3, 2, 1-kl] phenoxazine (XI) with the foregoing aromatic aldehydes afforded 3-benzylidenehydrazono-1, 2-dihydro-3H-pyrido [3, 2, 1-kl] phenoxazines (XII-XVI). On the other hand, application of acetyl chloride or benzoyl chloride to XI, 3-hydroxy-1, 2-dihydro-3H-pyrido [3, 2, 1-kl] phenoxazine (XX), 3-amino-1, 2-dihydro-3H-pyrido [3, 2, 1-kl] phenoxazine (XXIII), and 1, 2-dihydro-3H-pyrazino [3, 2, 1-kl] phenoxazine (XXVI) in pyridine afforded the corresponding acetyl compounds (XVIII, XXI, XXIV, XXVII) or benzoyl compounds (XIX, XXII, XXV, XXVIII). When phenyl isocyanate and phenyl isothiocyanate were reacted with XXVI, 3-phenylcarbamoyl-1, 2-dihydro-3H-pyrazino [3, 2, 1-kl] phenoxazine (XXIX) and 3-phenylthiocarbamoyl-1, 2-dihydro-3H-pyrazino [3, 2, 1-kl] phenoxazine (XXX) were obtained.
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