Acylation of toluidines with 1,4-dimethylcyclohex-3-enecarbonyl chlorides

Abstract

Amide group is a component of various compounds, which are of great practical importance. Organic compounds containing the amide groups in the molecule are obtained mainly by the acylation of amines with carboxylic acids and their derivatives. In the literature, there is enough information on the acylation of amines with aromatic carboxylic acids [1], their chlorides [2], esters [3], and anhydrides [4]. Among the acylating agents the carboxylic acid chlorides are the stronger electrophilic reagents. However, there are no published data on the acylation of amines with carboxylic acid chlorides of the cyclohex-3-ene series. We first investigated the acylation of amines with alicyclic carboxylic acid chlorides. Recently, the acylation of aromatic monoand diamines as well as functionally substituted monoamines have been studied [5, 6]. Continuing research in this area, we studied the acylation of toluidine with cyclohex-3-enecarbonyl chloride III. 1,4-Dimethylcyclohexenecarboxylic acid I was synthesized by us via the Diels–Alder condensation of isoprene with methacrylic acid [7]. The isomers separation was performed by the method [8]. DOI: 10.1134/S1070363213010325