An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters

作者：Kumar Padam Praveen^*; Reddy Y Dathu; Kumari Y Bharathi; Devi B Rama; Dubey P K

来源：Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry , 2014, 53(4): 392-398.

• Phthalic anhydride
• maleic anhydride
• succinic anhydride
• Mg turnings

Phthalic, maleic and succinic anhydrides have been reacted with aromatic amines to obtain the corresponding monoacid monoamides. The latter have been each transformed into the corresponding cyclic imide derivatives by treating with SOC2. Alternatively, anhydrides have been reacted with methanolic KOH to obtain monomethyl ester derivatives which on reaction with aromatic amines in the presence of EDC, HC1 and HOBt give cyclic imide derivatives. Reaction of monoacid monoamides independently, with SOC2 at 0-5 degrees C give the Monoamide monoester derivatives. Treatment of monoamide monoester of malic anhydride with NaBH4 leads to the unusual reduction of C=C grouping as well as the carbonyl group ofthe ester group to from monoamide monoalcohol of succinic anhydride. Preparation of monoamide monoalcohol of succinic anhydride can also be achieved by chemoselective reduction of monoamide monoester of malic anhydride with Mg turnings yielding monoamide monoester of succinic anhydride followed by reduction of the latter with NaBH4.

• 出版日期2014-4