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Synfacts 2010(8): 0877-0877
DOI: 10.1055/s-0030-1257857
DOI: 10.1055/s-0030-1257857
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Substituted Indoles Using Flow Microreactors
B. Wahab, G. Ellames, S. Passey, P. Watts*
University of Hull and Sanofi-Aventis, Alnwick, UK
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. Juli 2010 (online)
Significance
The synthesis of various indoles with throughputs of up to 20.1 mgh-¹ per single channel reactor has been developed. When ketones 1 reacted with phenylhydrazine (Fischer synthesis) via [3,3]-sigmatropic rearrangement, substituted indoles 2 were obtained in moderate to excellent yields. The substrate scope was moderately studied. Three different conditions were investigated; homogenous catalysis (method 1); neat acid catalysis (method 2), and heterogeneous catalysis (method 3). The heterogeneous approach was shown to be the most efficient.