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Synthesis 1994; 1994(1): 93-96
DOI: 10.1055/s-1994-25412
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New Synthesis of 2-Aryl- and 2-Hetarylpyrroles from 1-Propargylbenzotriazole

Alan R. Katritzky* , Jianqing Li, Mikhail F. Gordeev
  • *Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville Fl 32611-2046, USA
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Publication Date:
17 September 2002 (online)

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1-(3-Lithiopropargyl)benzotriazole reacts with N-tosylarylimines to give adducts which undergo cycloelimination on treatment with ethanolic sodium hydroxide to afford 2-aryl- and 2-hetarylpyrroles in 45-60% yields. Treatment of 1-(1,3-dilithiopropargyl)benzotriazole successively with 1 equivalent of an alkyl halide followed by N-tosyl(1-naphthyl)imine and then ethanolic sodium hydroxide gives the corresponding 5-alkyl-2-(1-naphthyl)pyrroles in 43-56% yields.