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Synthesis 1997; 1997(12): 1451-1456
DOI: 10.1055/s-1997-1360
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A New Preparation of Functionalized 3-Alkanoylpyrroles and 7-Oxoisoindoles

Jérôme Boëlle, Raphaël Schneider, Philippe Gérardin, Bernard Loubinoux*
  • *LERMAB, Laboratoire de Chimie Organique-Microbiologie, Université Henri Poincaré, Nancy-I. Faculté des Sciences, BP 239, F-54506 Vandoeuvre-les-Nancy, France, Fax +33(3)83912554; E-mail: Bernard.Loubinoux@lermab.u-nancy.fr
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Publication Date:
31 December 2000 (online)

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Reaction of the ethylene acetals of β-nitroenones 3 with isocyano-acetates followed by acidic hydrolysis allowed the synthesis of 3-alkanoylpyrrole-2-carboxylates 9a-f and 7-oxo-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylates 9g-i in good yield. 3-Alkanoyl-4-nitropyrroles 11a,b were obtained using 3 and tosylmethyl isocyanide.

β-nitroenones ethylene acetals - isocyanoacetates - tosylmethyl isocyanide - 3-alkanoylpyrrole-2-carboxylates - 7-oxoisoindole-1-carboxylates - 3-alkanoyl-4-nitropyrroles