80818-21-9Relevant articles and documents
Substituent effects on the regioselectivity of maleamic acid formation and hydrogen chloride addition to N-aryl maleimides
Faturaci, Yeliz,Coskun, Necdet
, p. 749 - 758 (2013/02/25)
Itaconic anhydride reacts with aryl amines to give a substituent controlled equilibrium mixture of regioisomeric (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4- (arylamino)but-2-enoic acids. Electron-donating groups favor nucleophilic attack on C-5 carbonyl, while the presence of electron-withdrawing groups enhances the bias for attack on C-2 carbonyl. The treatment of (Z)-2-methyl- and (Z)-3-methyl-4-oxo-4-(arylamino)but-2-enoic acids with SOCl2-Et 3N in THF provided the corresponding maleimides in high yields while under the same conditions the maleic anhydride aryl amine addition products gave predominately the corresponding 3-chloro-1-arylpyrrolidine-2,5-diones and maleimides in substituent dependent ratio. TUeBITAK, 2012.
The Action of Amines on Citraconic Anhydride. X-Ray Crystal Structure of (Z)-2-Methyl-3-pyrrolidinocarbonylpropenoic Acid
Baydar, Ahmet E.,Boyd, Gerhard V.,Aupers, John,Lindley, Peter F.
, p. 2890 - 2894 (2007/10/02)
The reaction of citraconic anhydride with 15 primary and secondary amines gave mixtures of isomeric citraconamic acids (2) and (3), in which the former predominated.The more abundant isomers rearranged to the thermodynamically stable N-substituted (Z)-2-m
