Synthesis and antimicrobial activity of dialkyl-2-aryl-6-hydroxy-6-methyl-4-( p-toluenesulfonylaminoimino) cyclohexane-1,3-dicarboxylates

Abstract

Reaction of dialkyl-2-aryl-6-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxylates with tosylhydrazide proceeds via the alicyclic carbonyl group to give dialkyl-2-aryl-6-hydroxy-6-methyl-4-(p-toluenesulfonylaminoimino)cyclohexane-1,3-dicarboxylates. The antimicrobial activity of the synthesized compounds has been evaluated.It was established previously that b-cycloketols and their derivatives exhibit antimicrobial and anti-inflammatory activity [1,2]. It seemed interesting to study the reaction of dialkyl 2-aryl-6-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxylates with tosylhydrazine in order to synthesize new biologically active compounds.Diacetyl-substituted cycloketols are known to react with hydrazine to form the corresponding indazoles [3]. The reaction of dialkyl 2-aryl-6-hydroxy-6-methyl-4-oxocyclohexane-1,3-dicarboxylates (Ia -m) with tosylhydrazide with heating in EtOH produced dialkyl 2-aryl-6-hydroxy-6-methyl-4-(p-toluenesulfonylaminoimino)cyclohexane-1,3-dicarboxylates (IIa -m) ( Table 1). R = OCH 3 (Ia, b; IIa, b); OCH(CH 3 ) 2 (Ic, IIc); OC 2 H 5 (Id -i, IId -i);

Syntheses and some features of five new cyclohexane-1,3-dicarboxylates with multiple stereogenic centers

“…The methods of further modification of the thus prepared cyclohexanones with mono-or polyfunctional nucleophiles are also well studied [20][21][22][23][24][25][26][27][28]. For instance, it was found that reactions of hydroxylamine [9], hydrazine [23,24], ethylenediamine [27], ethanolamine [8,26,27], ethylene glycol [4], substituted aromatic amines [20,21,25], tosylhydrazide [22] and benzidine [28] with diethyl-4-hydroxy-4-methyl-6-oxo-2-phenylcyclohexane-1,3-dicarboxylate give isoxazole, imidazole and 1,3-dioxolane rings, Schiff base condensation products, etc. Moreover, in some cases the cyclization processes depend on temperature, i.e.…”

Synthesis and Spectral Studies of R(2),C(4)-Bis(Tert-Butoxycarbonyl)-C(5)-Hydroxy-T(5)-Methyl-T(3)-Phenyl Cyclohexanone and Their Biological Activity

“…Heterocyclic compounds are an important class and have been found as a crucial structural core in natural and synthetic drugs [12]. In recent years, β-keto esters have displayed a number of important biological properties such as bactericidal, fungicidal, and anti-inflammatory activities [13][14][15]. Antioxidants have gained a lot of importance because of their potential prophylactic and therapeutic activities against many diseases.…”