PEG-600 mediated simple, efficient and eco-friendly synthesis of N-substituted imides and chemo selective C =C reduction

Green Chemistry Letters and Reviews

Padam Praveen Kumar¹ 

关键词: PEG-600;    anhydrides;    N-substituted imides;    chemoselective reduction;    Mg turnings;   

DOI  :  10.1080/17518253.2011.571720

学科分类：化学（综合）

来源: Taylor & Francis

【 摘 要 】

Phthalic anhydride 1 was reacted with aromatic primary amines 2 in acetic acid at room temperature to yield mono acid mono amide derivatives 3. The latter were each transformed into the corresponding imides 4 by heating in the green solvent PEG-600 at 60°C high yields and in high purity in short reaction times involving a dehydrative ring closure. The above reaction of 1 with 2 in acetic acid was extended to succinic anhydride 5 and maleic anhydride 8 resulting in open chain compounds 6 and 9, respectively. The latter were cyclized, once again in the green solvent PEG-600, to the corresponding imides, i.e. succinimides 7 and maleimides 10, respectively. Each of the imides 4, 7, and 10 could be reconverted to the corresponding open chain compounds 3, 6, and 9 by heating in ethanolic KOH. Simple hydrolysis of imides 4, 7, and 10 with aq.H3PO4 yielded the corresponding dicarboxylic acids 11, 12, and 13, respectively. Treatment of maleic amide 9 and maleicimide 10 with Mg in EtOH under reflux gave th...

【 授权许可】

Unknown