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Approaches to the Construction of Substituted 4-Amino-1H-pyrrol-2(5H)-ones

Hassan Zali-Boeini*, Mehdi Mobin, Khadijeh Hajibabaei and Maryam Ghani

*Department of Chemistry, University of Isfahan, 81746-73441, Isfahan, Iran, Email: h.zalichem.ui.ac.ir

H. Zali-Boeini, M. Mobin, K. Hajibabaei, M. Ghani, J. Org. Chem., 2012, 77, 5808-5812.

DOI: 10.1021/jo3004309 (free Supporting Information)


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Abstract

Fully substituted 4-aminopyrrolones are easily accessed starting from imines, ketones, or α-bromophenyl acetonitriles. Imines are reacted with KCN/NH4Cl, whereas ketones are transformed to the desired α-amino nitriles using a modified Strecker reaction. Reaction with a suitable acyl halide produces the corresponding amides. Ttreatment of these amides with ethanolic KOH gives 4-amino-1H-pyrrol-2(5H)-one derivatives in good yields.

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Key Words

N-Heterocycles


ID: J42-Y2012-2240