2,6-DIMETHYL-4-NITROBENZOIC ANHYDRIDE (DMNBA): AN EFFECTIVE COUPLING REAGENT FOR THE SYNTHESIS OF CARBOXYLIC ESTERS AND LACTONES

作者：Shiina Isamu^*; Miyao Ryo

来源：Heterocycles, 2008, 76(2): 1313-1328.

• 2,6-Dimetho-4-nitrobenzoic Anhydride
• DMNBA
• 2-Methyl-6-nitrobenzoic Anhydride
• MNBA
• Carboxylic Ester

Various carboxylic esters are obtained at room temperature in excellent yields with high chemoselectivities from nearly equimolar amounts of carboxylic acids and alcohols using 2,6-dimethyl-4-nitrobenzoic anhydride with triethylamine by the promotion of 4-(dimethylamino)pyridine. The efficiency of the esterification is compared to those of other dehydrations using substituted benzoic anhydrides as coupling reagents. This method was successfully applied to the synthesis of threo-aleuritic acid lactone and the desired 17-membered ring compound was prepared in high yield at room temperature from the corresponding free trihydroxycarboxylic acid using 2,6-dimethyl-4-nitrobenzoic anhydride in the presence of 4-(dimethylamino)pyridine.

• 出版日期2008-11-1