58668-65-8Relevant academic research and scientific papers
Hydrolysis of Acyl Derivates of Malonaldehyde Dianil. II. Aminolysis and Alcoholysis of Acyl Derivates of Malonaldehyde Dianil and β-Arylaminoacrolein
Ono, Machiko,Tamura, Shinzo
, p. 1443 - 1452 (2007/10/02)
Aminolysis and alcoholysis reactions of β-arylaminoacrolein and its N-acyl derivates were studied.Acid-catalysed aminolysis of β-(N-benzoyl-p-toluidino)acrolein (III) occured at the β-position of III, accompanying the reversible interaction of the amine and the formyl group of III.In the reaction of III and amine in methanol under neutral conditions, aminolysis at the β-position of III and alcoholysis of the amide carbonyl group of III proceeded in parallel; the latter reaction was catalysed by amine.In either case, no evidence of aminolysis at the amide carbonyl group of III was obtained.The reaction of the fotmyl group of III proceeded mainly when III and amine were reacted in benzene solution.Thus, 1-(N-benzoyl-p-methylphenylamino)-3-(p-chlorophenylimino)-1-propene (XII) was obtained when III and p-chloroaniline were reacted in benzene.Alkaline hydrolysis of XII afforded 1-(p-methylphenylamino)-3-(p-chlorophenylimino)-1-propene (XIII), an unsymmetrical malonaldehyd dianil.Aminolysis and alcoholysis reactions of 1-arylamino-3-arylimino-1-propene(malonaldehyde dianil) and its N-acyl-derivates were also studied.Alcoholysis occured at the amide carbonyl group of N-acyl derivates, while aminolysis occured at the 1-position except for the case of 1-(N-phenylcarbamoyl-p-methylphenylamino)-3-(p-methylphenylimino)-1-propene (XIV).Keywords--aminolysis; alcoholysis; β(N-benzoyl-p-toluidino)acrolein; β-(N-phenycarbamoyl-p-toluidino)acrolein; l-(N-benzoyl-p-methylphenylamino)-3-(p-methylphenylimino)-1-propene; l-(N-benzoyl-p-methylphenylamino)-3-(chlorophenylimino)-1-propene; 1-(p-methyphenylamino)-3-(p-chlorophenylimino)-1-propene; 1-(N-phenylcarbamoyl-p-methylphenylamino)-3-(p-methylphenylamino)-3-(p-methylphenylimino)-1-propene
Hydrolysis of Aryl Derivates of Malonaldehyde Dianil. III
Ono, Machiko,Tamura, Shinzo
, p. 1453 - 1462 (2007/10/02)
The reaction sequence of hydrolysis of N-acyl derivates of malonaldehyde dianil was examined.Hydrichloric acid-catalysed hydrolysis occured at the imino group to form arylamine and β-(N-acylarylamino)acrolein; the latter compound is not stable in acid solution.In the case of 1-(N-phenylcarbamoyl-p-methylphenylamino)-3-(p-methylphenylimino)-1-propene, hydrolysis occured at both the imino and the carbamoyl groups.Buffer catalysed hydrolysis occured at the imino group, and the resulting β-(N-acylarylamino)acrolein and arylamine reacted to form β-arylaminoacrolein and N-arylamine.The aminolysis reaction was suppressed in hydrochloric acid-catalysed hydrolysis.Alkaline hydrolysis of N-acyl derivates of malonaldehyde dianil and of β-arylaminoacrolein occured at the amide carbonyl group except in the case of 1-(N-tosyl-p-methylphenylamino)-3-(p-methylphenylimino)-1-propene.N-tosyl-p-toluidine was obtained in this case.Keywords--hydrolysis; malonaldehyde dianil; β-arylaminoacrolein; 1-(N-acylarylamino)-3-arylamino-1-propene; β-(N-acylarylamino)acrolein; 1-(N-tosyl-p-methylphenyilamino)-3-(p-methylphenylimino)-1-propene; 1-(N-tosyl-p-methylphenylamino)-3-(p-methylphenyilimino-1-butene; β-(N-tosyl-p-toluidino)acrolein; 4-(N-tosyl-p-toluidino)-3-buten-2-one
