850148-32-2Relevant academic research and scientific papers
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.
α-chlorosuccinimides - A new source for maleimides and succinimides
Gǎinǎ, Constantin,Gǎinǎ, Viorica
, p. 655 - 661 (2007/10/03)
N-Arylmaleimides and N-arylsuccinimides were prepared by dehydrochlorination reaction of N-aryl α-chlorosuccinimides in the presence of a base and by reduction of 2-chlorosuccinimide in the presence of zinc, respectively. N-Aryl α-chlorosuccinimides were obtained by dehydration of N-aryl substituted maleamic acids in the presence of thionyl chloride. The structure of the synthesized compounds was confirmed by IR, 1H-NMR and 13C-NMR spectra.
