Twenty-four kinds of pyridazinone derivatives (II) were synthesized by the application of methyl or ethyl iodide, acetyl, benzoyl, or benzyl chloride, or 2-bromoacetophenone to 3, 6-dimethoxy-, 3, 6-diethoxy-, 3, 6-dimethoxy-4-methyl-, and 3, 6-diethoxy-4-methylpyridazine 1-oxides (I), and infrared and ultraviolet spectra of II were measured. Reactivity of these reagents decreased in the order of acetyl chloride, benzoyl chloride, methyl and ethyl iodide, and benzyl chloride. 1-Phenacy1oxy-3-alkoxy-6(1H)-pyridazi-nones (II_<13∼16>) were found to undergo decomposition by heat, alcohol, acid, and alkali to form 3-alkoxy-6(1H)-pyridazinones (IIIa, b, c) and phenylglyoxal (IV).

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Syntheses were carried out on 4-alkylthiazole-2-thiol, 4-phenylthiazole-2-thiol, and their derivatives substituting the thiol group in 2-position with alkyl, aryl, and carboxylic acid ester group, and introduction of ethylthio and phenylthio group into the 5-position. Relationship between the chemical structure of these compounds and their antifungal activity is discussed.

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2-Thioxo-4-oxo-5-thiazolidineacetic acid and its esters were synthesized by a new method of reacting maleic acid or its esters with dithiocarbamic acids. Structure of the products was proved from ultraviolet and infrared absorption spectra.

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2-Thioxo-4-oxo-5-thiazolidineacetamide derivatives were prepared by the new method of reacting maleinamide and N-substituted maleinamides or maleimides with dithiocarbamic acids. Structure of the products thereby formed was established through ultraviolet and infrared absorption spectra.

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Reaction of 2-(2-aminoethylamino) ethanol, aniline, and p-nitroaniline with mesyl chloride and pyridine afforded normal mesylated compounds but the same reaction of o-aminophenethyl alcohol (IV), anthranilic acid (V), and 2-(2-thenylamino) pyridine (VI) gave interesting reaction products (VIII, XI, XIII).

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L-Gulonolactone (I) was condensed with benzaldehyde to afford mono- and di-O-benzylidene-L-gulonolactone. Mono-O-benzylidene-L-gulonolactone (II) was not oxidized by periodic acid, while its amide was oxidized extremely slowly by periodic acid. II was reduced by sodium borohydride to yield 2, 4-O-benzylidene-D-sorbitol. Therefore, the structure of II was established as 3, 5-O-benzylidene-L-gulonolactone. Di-O-benzylidene-L-gulonolactone (III) was partially hydrolyzed by acid to II. III did not react with ammonia in methanol and was recovered from the reaction mixture. Based on the result of acid hydrolysis of III and from the conformational consideration, it was concluded that III is 2, 6 : 3, 5-di-O-benzylidene-L-gulonolactone.

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Synthesis of nitrogen-heterocyclic condensed γ-pyrone derivatives was attempted from 6-quinolinol by two different routes, and two new compounds, 1H-pyrano[3, 2-f]quinolin-1-one and 3-methyl-1H-pyrano[3, 2-f]quinolin-1-one, were prepared. The same reaction was carried out with 8-quinolinol but the cyclization reaction did not progress and the objective compounds were not obtained. The same reaction of 6, 8-quinolinediol afforded 6-hydroxy-3-methyl-1H-pyrano[3, 2-f]quinolin-1-one.

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A series of salicylic acid derivatives and allied compounds, synthesized in order to lower the toxicity, increase the pharmacologica1 activity, and increase the solubility, were tested for toxicity and analgesic activity. N, N-Dimethyl-2-(o-methoxybenzamido)-acetamide and few other compounds were found to satisfy these objectives.

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Examination of alkaloidal constituents of the heartwood and bark of Magnolia obovata THUNB. (Japanese name "Honoki")(Magnoliaceae), collected in the Hida-Takayama district, Gifu Prefecture, led to the isolation of secondary alkaloids michelarbine (III) and anonaine (IV), a tertiary alkaloid liriodenine (II), and water-soluble quaternary alkaloids magnocurarine (I) and magnoflorine (V).

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Examinations were made on the alkaloids contained in the tree bark of Neolitsea sericea (BLUME) KOIDZ. (Lauraceae). Besides (+)-laurolitsine (I), (+)-boldine (II), (-)-roemerine (IX), and (+)-litsericine (XI) found in the leaves, four kinds of phenolic and three kinds of non-phenolic bases were isolated. These were identified as the phenolic bases (+)-actinodaphnine (III), (+)-N-methylactinodaphnine (IV), (+)-laurotetanine (V), and (+)-N-methyllaurotetanine (VI), and non-phenolic bases (-)-nuciferine (VII), (-)-anonaine (VIII), and liriodenine (X).

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The new alkaloid, litsericine, C₁₇H₂₁O₃N, isolated from Neolitsea sericea (BLUME) KOIDZ. (Lauraceae), was given the formuLa (I) having a ring structure of hexahydroproaporphine type.

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Coloration reaction of 2', 3', 6', 7'-tetrahydroxyfluoran derivatives with metal ions is bathochromic and examination was made on the use of these compounds as an indicator of metal ions like Pb, Hg, Bi, Ce, La, Cd, Co, Ni, Cu, Mg, Ca, and Ba chelate titration with 2', 3', 6', 7'- and 1', 3', 6', 8'-tetrahydroxyfluoran derivatives as indicators was carried out using metal solutions of pH 3∼4 (ammonium acetate buffer), over pH 3 (dil. HNO₃), pH 4∼6 (hexamine buffer), pH 10 (NH₄OH·NH₄Cl buffer), over pH 10 (NH₄OH soln.), and above pH 10 (NaOH soln.). The halogen derivatives (Cl, Br, I) of 3', 6', 7'- and 3', 6', 8'-trihydroxyfluoran derivatives effected clearer color change by titration due to the auxochromic effect of the halogen atom, and sensitivity of the color increased in the order of Br, Cl, and I, and the positions if the substituted halogens and hydroxyl also affected sensitivity to coloration, sensitivity decreasing in the order of 4'-, 2'-, 2', 4'- halogeno-3', 6', 7'- and 2', 4'-, and 2', 4'-halogeno-3', 6', 8'-trihydroxyfluoran derivatives. In the hydroxyfluoran-complexone compound, bathochromic coloration occurred in the increasing order of 2', 3', 6', 7'-hydroxyfluoran-imindiacetic acid, aminoacetic acid-complexone, and hydroxyfluoran.

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3-(Diphenylhydroxymethyl) pyrrolidine derivatives (II, XI) were synthesized for anticipation of anti-acetylcholine action. II and XI were obtained by the Grignard reaction of ethyl 1-ethyl-3-pyrrolidinecarboxylate (I) and ethyl 1-ethyl-2-methyl-3-pyrrolidinecarboxylate (X), respectively, with phenylmagnesium bromide. I was obtained by oxidation of 1-ethyl-3-pyrrolidinemethanol with chromium trioxide and subsequent esterification. X was obtained from diethyl 2-methyl-4-oxo-1, 3-pyrrolidinedicarboxylate (V) via VI, VII, VIII, and IX. X should occur in stereoisomers in which the methyl in 2-position and ethoxycarbonyl in 3-position are in cis or trans configuration and this fact was confirmed by gas chromatography and other methods.

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1-Ethyl- or 1-methyl-2-meithyl-2-pyrroline (III : R=C₂H₅ or CH₃, R'=CH₃) was ethoxycarbonylated in dehyd. ether, utilizing its enamine reaction. Subsequent reduction afforded ethyl 1-ethyl-2-pyrrolidineacetate (V), in which the ethoxycarbonyl group was introduced into the position β to the exocyclic C=C, from the 1-ethyl compound (III), and the cis compound (Xb) of ethyl 1, 2-dimethyl-3-pyrrolidinecarboxylate, in which the ethoxycarbonyl group was introduced into the position β to the endocyclic C=C, from the 1-methyl compound. The same reaction in chloroform caused substitution of ethoxycarbonyl group into the position β to the exocyclic C=C in the 1-methyl compound (III : R=R'=CH₃) and ethyl 1 methyl-2-pyrrolidineacetate (XIV) was obtained.

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