Azlactone compound and method for preparation thereof

Abstract

Compounds represented by formula (II): wherein M is a hydrogen atom, sodium, potassium, or lithium; P is a hydrogen atom, an alkyl group, and the like; and the wavy line indicates a cis form, a trans form, or a mixture thereof for the double bond to which it is attached, may be prepared by hydrolyzing a compound represented by formula (I), or a salt thereof: wherein R 1 and R 2 are the same or different and each is an alkyl group, or R 1 and R 2 together with the adjacent nitrogen atom may form an aliphatic heterocycle, and P and the wavy line are as defined above, in the presence of alkali metal hydroxide.

1 . A method of making a compound represented by formula (II): 
       
         
           
           
               
               
           
         
       
       wherein:
 M is a hydrogen atom, sodium, potassium, or lithium; 
 P is a hydrogen atom, an alkyl group, an alkenyl group, an aryl group optionally having one or more substituents, an aralkyl group optionally having one or more substituents, or a haloalkyl group; and 
 a wavy line indicates a cis form, a trans form, or a mixture thereof for the carbon-carbon double bond to which it is attached, 
 said method comprising: 
 (1) hydrolyzing a compound represented by formula (I), or a salt thereof: 
 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1  and R 2  are the same or different and each is an alkyl group, or R 1  and R 2  may be bonded together to form an aliphatic heterocycle together with the adjacent nitrogen atom; and 
 P and a wavy line are as defined above, 
 in the presence of alkali metal hydroxide, to obtain said compound of formula (II). 
 
     
     
         2 . The method of  claim 1 , wherein P is a methyl group, an ethyl group, a benzyl group, a p-tolyl group, or a p-chlorophenyl group. 
     
     
         3 . The method of  claim 1 , wherein M is sodium or potassium. 
     
     
         4 . The method of  claim 1 , wherein P is a methyl group, an ethyl group, a benzyl group, a p-tolyl group, or a p-chlorophenyl group; and M is sodium or potassium. 
     
     
         5 . The method of  claim 1 , which is performed in a solvent other than an alcohol solvent. 
     
     
         6 . The method of  claim 1 , which is performed in a solvent other than an alcohol solvent, and wherein P is a methyl group, an ethyl group, a benzyl group, a p-tolyl group, or a p-chlorophenyl group. 
     
     
         7 . The method of  claim 1 , which is performed in a solvent other than an alcohol solvent, and wherein M is sodium or potassium. 
     
     
         8 . The method of  claim 1 , which is performed in a solvent other than an alcohol solvent, and wherein P is a methyl group, an ethyl group, a benzyl group, a p-tolyl group, or a p-chlorophenyl group; and M is sodium or potassium. 
     
     
         9 . The method of  claim 1 , wherein said alkali metal hydroxide comprises at least one alkali metal hydroxide selected from the group consisting of sodium hydroxide, potassium hydroxide, lithium hydroxide, and mixtures thereof. 
     
     
         10 . The method of  claim 1 , wherein said alkali metal hydroxide comprises at least one alkali metal hydroxide selected from the group consisting of sodium hydroxide, potassium hydroxide, and mixtures thereof. 
     
     
         11 . The method of  claim 10 , wherein P is a methyl group, an ethyl group, a benzyl group, a p-tolyl group, or a p-chlorophenyl group. 
     
     
         12 . The method of  claim 10 , wherein M is sodium or potassium. 
     
     
         13 . The method of  claim 10 , wherein P is a methyl group, an ethyl group, a benzyl group, a p-tolyl group, or a p-chlorophenyl group; and M is sodium or potassium.