Treatment of salicylidene-anils with potassium cyanide in acetic acid affords 1:1 adducts shown to be the hydrocyano derivatives. When the reaction is conducted in alcohol, salicylidene derivatives of 2-amino-3-arylaminobenzofurans or α-arylamino-o-hydroxyphenylacetamides are formed depending on the molar ratio of the reactants. The formation of the products and the previously reported structures are discussed.
Treatment of a-phenylthiocarbamoyl acetyl acetone (1) with aromatic diazonium salts effects acetyl cleavage with the formation of 2-methyl-I-phenylthiocarbamoylglyoxal arylhydrazones (2a-c), which afford the anilinopyrazoles (5a-c) and the phenylimino-2- pyrazolines (6a-c) on treatment with hydrazine or phenyl hydrazine respectively.
Treatment of diethyl a-phenylthiocarbamoyl malonate with aryl diazonium salts gave diethyl (arylazo)(phenylthiocarbamoyl) malonate which afford the 7-phenyl-5-(arylazo)- 2,3,7-triazabicyclo[3,2,0]hept-I-ene-4,6-dione (9a, b) and its 3-phenyl derivatives (9c, d) with hydrazines and phenyl hydrazine respectively
Treatment of ethyl α-phenylthiocarbamylacetoacetate (1) with aromatic diazonium salts effects acetyl cleavage with the formation of ethyl α-phenylthiocarbamylglyoxalate arylhydrazones derivatives (2 a-e) which afford the anilinopyrazolones (5) and (7) on treatment with hydrazine or phenylhydrazine. The pyrazolones 5 a-e undergo aminoalkylation with formaldehyde and piperidine to give the N-Mannich bases 7 a-e, also obtained by treating the N-hydroxymethyl derivatives (9 a-e) with piperidine.
The 5-arylazo-1-methyl-2-benzyl-2-imidazolin-4-ones (1 a-c) undergo ring cleavage with 1% aqueous sodium hydroxide solution affording α-arylhydrazono-phenacetyl-sarcosine amide (2). Prolonged heating of 1 and 2 with the same reagent yields the cyanamide (3). On the other hand, when 1 a-c were refluxed with acetic acid the triazinones (4) were obtained. The latter adds one mole of Grignards reagent to yield the 5-hydroxy-1,2,4-triazine derivatives (5).