Journal of Synthetic Organic Chemistry, Japan

Synthetic Studies of 1α-Hydroxyvitamin D₃ and its Related Compounds

In Search of New Synthetic Analogues of the Active Metabolite of Vitamin D₃ : 1α, 25- (OH) ₂-D₃

Chikara KANEKO

1975 Volume 33 Issue 2 Pages 75-94
Published: February 01, 1975
Released on J-STAGE: January 22, 2010

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.33.75

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Syntheses and Reactions of Azonia-aromatic Compounds

Mitsuhiko HIDA

1975 Volume 33 Issue 2 Pages 95-128
Published: February 01, 1975
Released on J-STAGE: January 22, 2010

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.33.95

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Some Reactions and Properties of Cyanobiguanide

Eiichi ICHIKAWA, Kazumi TANAKA, Keijiro ODO

1975 Volume 33 Issue 2 Pages 129-135
Published: February 01, 1975
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.33.129

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Cyanobiguanide (1) is a linear cyanamide trimer with triazapentadiene structure. Its reactions were invesigated and compared with those of cyanamide and dicyandiamide.
I was hydrolyzed in 46 N hydrochloric acid to give guanylbiuret (2) hydrochloride at 2070°C, but in concentrated acid, ammeline salt was the main product. (2) was identical with an authentic sample obtained by the reaction of I-thioallophanic acid -S-methyl ester with guanidine.
The imidoether derivative of (1), biguanyl-O-methylisourea (3) salt was synthesized by the addition of methanol to (1) in the presence of excess hydrogenchloride. Some properties of (3) were investigated. 3-Amino-5-guanidino-1, 2, 4-triazole salt and 5-aminotetrazole were obtained in lower yields by the reactions of (1) with hydrazine salt and hydrogen azide.
The cyano group of (1) seems to be less reactive than that of cyanamide and dicyandiamide in the reactions with methanol, hydrazine salt and hydrogen azide.
Catalytic reduction of (1) using Pd gave formoguanamine in aqueous solution.

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Synthetic Study of Cyanoaminocarbonic Acid Derivatives (Part 4)

Takayuki SUYAMA, Keijiro ODO

1975 Volume 33 Issue 2 Pages 136-140
Published: February 01, 1975
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.33.136

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Spontaneous reactions of methylmercaptocarbonyl-cyanamide (MCC) and some chemical properties of its related compounds were investigated. It was found that MCC was converted to its dimer, 1-cyano-1, 3-di- (methylmercaptocarbonyl) -guanidine (d-MCC), when it was allowed to stand for a long time in cristalline form or in ethereal solution. On the other hand, di- (methylmercaptocarbonyl) -cyanamide (1) was formed when MCC was treated in acetone as solvent or warmed by itself. The structure and chemical properties of d-MCC were also discussed. d-MCC was easily hydrolyzed in hot water and 1-cyano-3-methylmercapto-carbonyl-guanidine (4) was obtained, while methylmercaptocarbonyl-urea (3) and 1-carbamoyl-3-methyl-mercaptocarbonyl-guanidine (2) salt were yielded in the presence of acid. Heating of d-MCC resulted in rearrangement of the methylmercaptocarbonyl group and gave 1-cyano-3, 3-di- (methylmercaptocarbonyl) -guanidine (5), which was easily converted to di- (methylmercaptocarbonyl) -amide (6) and dicyanamide (7) salt in alkaline medium.

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Study of Antipolluted Pigments

An Approach to Nontoxic and Related Pigments

Teijiro KITAO

1975 Volume 33 Issue 2 Pages 141-150
Published: February 01, 1975
Released on J-STAGE: November 13, 2009

DOIhttps://doi.org/10.5059/yukigoseikyokaishi.33.141

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