New information on the Hofmann reaction Communication 5. Reaction of amides of n-acylated?-plperonyl-?-alanines with alkaline hypobromites

Abstract

1. The Hofmann Reaction has been carried out with the amides of N-benzoyl, N-acetyl and N-carbomethoxy β-Piperonyl-s-alanine under different conditions (heating to 65° and 80°). 2. It has been shown that in all cases the reaction mechanism is the same as that which occurs with the amides of of N-acylated β-phenyl-s-alanines. The mechanism may be considered a general one for amides of N-acylated aminoacids of the aromatic series. 3. In all three cases 5-piperonylglyoxalidone, 5-piperonyl-l,3,4-oxadiazol-2(3H)-one and piperonylic acid were separated from the reaction-mixture; in addition the reaction with N-benzoyl-s-piperonyl-s-alanine yielded 1-N-benzoyl-5-piperonylglyoxalidone. 4. It has been shown that the separation of 1-N-benzoyl-5-piperonyglyoxalidone takes place readily under the conditions used by Rodionov and Zvorykina for amino-acids if the aliphatic series (heating to 65°), and the separation of piperonylic acid under the more drastic conditions (heating to 80° ) which we have previously used (reaction proceeding further ). 5. When the Hofmann Reaction was carried out on N-acetyl-s-piperonyl-s-alanine, a bromine-containing compound of composition C12H13O4N2Br was separated.