Synthesis of N-sugar-substituted phthalimides and their derivatives from sugar azides and phthalic anhydride.
N-Sugar-substituted phthalimides and tetrachlorophthalimide derivatives can be prepared in good yields under essentially neutral conditions. Mixing a sugar azide, NaI, Me3SiCl, phthalic or substituted phthalic anhydride and tetrabutylammonium iodide as catalyst in acetonitrile at rt or 60 degrees C, afforded 12 imides in 83-95% yields.
Zhang
Su-Na
SN
Department of Chemical Biology, School of Pharmaceutical Sciences, National Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, China.
Li
Zhong-Jun
ZJ
Cai
Meng-Shen
MS
D001386:Azides / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D015394:Molecular Structure; D010796:Phthalic Anhydrides / Q000737:chemistry*; D010797:Phthalimides / Q000138:chemical synthesis* / Q000737:chemistry
D001386:Azides; D002241:Carbohydrates; D010796:Phthalic Anhydrides; D010797:Phthalimides