Tetrahydroquinoline derivatives and a process of preparation thereof

Abstract

The present disclosure provides tetrahydroquinoline derivatives of Formula (I) wherein X 1 and X 2 each, independently, are oxygen or sulphur; R 1 is a lower alkoxy, or an optionally substituted aryl group; R 2 is selected from a group consisting of hydrogen, lower alkyl, haloalkyl, or an amino group; R 3 and R 4 each, independently, are hydrogen, or lower alkyl groups; and R5 and R6 are optionally substituted aryl groups. The present disclosure also provides a method for making the compound of Formula (I).

1 - 12 . (canceled) 
     
     
         13 . A method of making a compound of Formula (I) and isomers and pharmaceutically acceptable salts thereof: 
       
         
           
           
               
               
           
         
         wherein X 1  and X 2  each, independently, are oxygen or sulphur; 
         R 1  is a lower alkoxy, or an optionally substituted aryl group; 
         R 2  is selected from a group consisting of hydrogen, lower alkyl, haloalkyl, and an amino group; 
         R 3  and R 4  each, independently, are hydrogen, or lower alkyl groups; and 
         R 5  and R 6  are optionally substituted aryl groups, the method comprising sonicating a combination of dimedone, a substituted benzaldehyde, and a reactant comprising an active methylene group, in presence of a catalyst to obtain the compound of Formula (I). 
       
     
     
         14 . The method according to  claim 13 , wherein the reactant comprising the active methylene group is a compound of Formula (III). 
       
         
           
           
               
               
           
         
         wherein, X is an ester or a cyano group; R 7  is selected from a group consisting of lower alkyl, haloalkyl, and an optionally substituted aryl group. 
       
     
     
         15 . The method according to  claim 14 , wherein X is a methoxycarbonyl or an ethoxy carbonyl group. 
     
     
         16 . The method according to  claim 14 , wherein R 7  is a substituent selected from a group consisting of methyl, ethyl, trifluoromethyl, phenyl, tolyl and a bromophenyl group. 
     
     
         17 . The method according to  claim 13 , wherein the substituted benzaldehyde is one of 4-(phenylsulfonyl) benzaldehyde or 4-tosylbenzaldehyde. 
     
     
         18 . The method according to  claim 13  further comprising, sonicating the combination of dimedone, substituted benzaldehyde, and the reactant comprising the active methylene group, in presence of ammonium acetate and ethanol. 
     
     
         19 . The method according to  claim 13 , wherein the catalyst is chitosan decorated copper nanoparticles (CS/CuNPs). 
     
     
         20 . The method according to  claim 13 , wherein the combination of dimedone, substituted benzaldehyde, and the other reactant comprising the active methylene group is sonicated at a frequency range of 20-40 Hz for a period of 20 to 30 minutes.