RESUMO
The reaction of alpha-diketones; namely, acenaphthenequinone, isatin, naphtho [2, 1-b] furan-1,2-dione and 5, 6-dihydrocyclopent [Fg] acenaphthylene-1,2-dione with dialkyl phosphites in the presence of aluminum oxide as catalyst was undertaken to give the corresponding alpha-hydroxyphosphonates
Assuntos
Química , Óxido de AlumínioRESUMO
Methods known for the preparation of 3-hydroxy-4-methoxytetraphenyl-methane la are indirect and lengthy. During our work on the reaction of alkyl phosphites with 4-triphenylmc-thyM,2-benzoquinone [II], we endeavoured the synthesis of [la] by the action of diazomethane on 3, 4-dihyd-roxytetraphenylmethane [Ib]
RESUMO
Quinoline having aminomethyl-or nitro-group in their nucleus exhibit marked pharmacological properties. Such compounds possess distinguished antimalarial[1], amoebicidal [2-4], acaricidal [5] and antispasmodic [6] activities. It seems, therefore of interest to synthesize some new quinolinol derivatives bearing both the two aforementioned groups for pharmacological evaluation. Although 6-hydroxy-8-nitroquinoline [1] retards several reactions typical of phenols [c.f. experimental], it undergoes aminomethylation under the Mannich reaction conditions [1] to give the Mannich base derivatives IIa-e. Thus, when nitroquinolinol [I] was allowed to condense with paraformaldehyde and a secondary amine in dioxan, the corresponding 5-aminomethyl derivatives IIa-e were isolated in good yield as solid free bases. The amines used were dimethylamine, diethylamine, diethanolamine, piperidine and morpholine. The same products IIa-e were also isolated when the reaction was carried using two mole-equivalents of both the secondary amines and paraformaldehyde mole of the nitroquinolinol I. Adducts IIa-e gave the correct analytical values. They respond positively to the ferric chloride colour reaction and soluble in cold 10 percent sodium hydroxide solution