The reactions of some 1,1-dialkylhydrazines with unsaturated and bromo aliphatic acids

Abstract

Various 1,1-dialkylhydrazines are alkylated by propiolic acid or 2- or 3-halopropenoic acids to give (E)-3-(1,1-dialkylhydrazin-1- io)propenoates.    

3-Bromopropionic acid reacts with N-aminomorpholine to give 1-amino-1-(2-carboxyethyl)-morpholinium bromide (11), with N- aminopiperidine to give bis(1-aminopiperidinium) 2-oxo-1-aza-5- azoniaspiro[4,5]decane tribromide (10), with 1,1-diethylhydrazine to give 1,1-diethyl-3-oxopyrazolidinium bromide (9) while with 1,1- dimethylhydrazine the 1 : 1 adduct of 3-(1,1-dimethylhydrazin-1- io)propionate (5a) and 1-(2-carboxyethyl)-1,1-dimethylhydrazinium bromide (8a) is obtained. The reaction of 1,1-dimethylhydrazine with methyl propiolate, methyl propenoate and itaconic acid gives (1,1- dimethylpyrazol-1-ium)-3-olate (4), (1,1-dimethyl-2-pyrazolin-1-ium)-3- olate (1a) and (1,1-dimethyl-3-oxopyrazolidin-1-io-4-yl)acetate (7) respectively. 1,1-Dimethylhydrazine reacts with ethyl 3-bromopropionate to give both 1-(2-ethoxycarbonylethyl)-1,1-dimethylhydrazinium bromide (8b) and (1,1-dimethyl-2-pyrazolin-1-ium)-3-olate (1a) while its reaction with bromoacetic acid gives the 1 : 1 adduct of (1,1- dimethylhydrazin-1-io)acetate (5b) and 1-carboxymethyl-1,1- dimethylhydrazinium bromide (8c).