GB770498A - -a-acylamino--ß-amino-propio-nitrophenones and derivatives and process for their preparation - Google Patents

Abstract

The invention comprises (1) the preparation of compounds of the formula <FORM:0770498/IV(b)/1> or <FORM:0770498/IV(b)/2> wherein R and R1 each represent a hydrogen atom or an acyl, alkyl, aryl, sulphamoyl aryl, aralkyl or heterocyclic (e.g. thiazole, pyrimidine or pyridine) group, or R and R1 may be joined together with the nitrogen atom to form a heterocyclic ring such as a piperidine, pyrrolidine, thiazolidine or morpholine ring, and R11 is an alkyl, aryl or dihaloalkyl group, by adding ammonia or a primary or secondary amine of the formula HN(R).R1, wherein R and R1 are as defined above except that neither is an acyl group, to an alpha-acylamino acrylo-nitrophenone in the presence of an inert solvent, such as an aliphatic or aromatic hydrocarbon or an ester, ether, or alcohol, at a temperature of 0 DEG to 100 DEG C., and, when it is intended to produce compounds wherein R and/or R1 is an acyl group, treating the initial product with the chloride or anhydride of a carboxylic acid or the chloride of a sulphonic acid and (2) as new products the compounds of the above general formula which are prepared in the examples below. The acylation of the initial condensation product is suitably carried out either in the cold in the presence of a tertiary amine such as pyridine, ethylpiperidine, dimethylaniline or triethylamine, or by heating in the presence of an acidic compound as a catalyst, e.g. concentrated sulphuric acid or gaseous hydrochloric acid. Examples describe the preparation by the processes of the invention of the a -acetamino - b - p - sulphonamidophenylamino-; a -dichloroacetamino - b - p - sulphonamidophenylamino-; a - acetamino - b - phenylamino -; a - dichloroacetamino - b - (4 - morpholinyl) -; a - acetamino - b - amino -; a - acetamino - b - p - acetamino - benzenesulphonamido and a - dichloroacetamino - b - (2 - pyrimidyl) - amino -, propio - p - nitrophenones and N - bis-[21 - (11 - p - nitrobenzoyl - 11 - dichloroacetamino) - ethyl] - 2 - amino - thiazole and N-bis-[2 - (1 - p - nitrobenzoyl - 1 - acetamino) - ethyl]-isopropylamine.