Approaches to the construction of substituted 4-amino-1H-pyrrol-2(5H)-ones.
Fully substituted 4-aminopyrrolones are easily accessed via simple routes starting from imines, ketones, or α-bromophenyl acetonitriles. Imines were reacted with KCN/NH(4)Cl in aqueous ethanol to produce α-arylamino benzyl cyanides. On the other hand, ketones were transformed to the desired α-amino nitriles using a modified Strecker reaction. Then, α-amino nitrile precursors were allowed to react with a suitable acyl halide to produce the corresponding amides. Further treatment of these amides with ethanolic KOH converted them to highly substituted 4-amino-1H-pyrrol-2(5H)-one derivatives in moderate to excellent yields.
Department of Chemistry, University of Isfahan, 81746-73441, Isfahan, Iran. h.zali@chem.ui.ac.ir
Hassan
H
Zali-Boeini
Mehdi
M
Mobin
Khadijeh
K
Hajibabaei
Maryam
M
Ghani
D000577:Amides / Q000737:chemistry*; D000431:Ethanol / Q000737:chemistry*; D006878:Hydroxides / Q000737:chemistry*; D015394:Molecular Structure; D017680:Potassium Compounds / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D006878:Hydroxides; D017680:Potassium Compounds; D011758:Pyrroles; D000431:Ethanol; C029943:potassium hydroxide