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Water‐Promoted Ring‐Opening Reactions of N ‐Substituted Saccharins and Phthalimides by Amines
Author(s) -
Bai Lisha,
Zhang Xuan,
Ma Ning
Publication year - 2014
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201400253
Subject(s) - chemistry , phthalimides , steric effects , ring (chemistry) , amine gas treating , hydrolysis , medicinal chemistry , benzoic acid , organic chemistry , phthalimide
The reactions of N ‐substituted saccharins and phthalimides with amines were promoted by water. Various o ‐sulfamoyl benzamides and N , N′ ‐disubstituted phthalamides were prepared in moderate to good yields. These reactions have prominent advantages, such as short reaction time, less by‐products and simple isolation of the products. Water can probably stabilize the reaction intermediates and facilitate precipitation of the ring‐opening products. When steric hindrance arose, hydrolytic compounds, either free acid or salts of the acids, were obtained. Possible reason for the formation of amine salts of o ‐sulfamoyl benzoic acids was proposed.