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DOI: 10.1055/s-2006-955564
Synthesis of Trifluoromethyl Pyrroles
N. Zanatta*, J. M. F. M. Schneider, P. H. Schneider, A. D. Wouters, H. G. Bonacorso, M. A. P. Martins, L. A. Wessjohann
Universidade Federal de Santa Maria, Brazil and Leibniz Institute of Plant Biochemistry, Halle/Saale, Germany
Publication History
Publication Date:
22 November 2006 (online)
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Significance
The regioselective synthesis of 4-amino- or 4-alkoxy-substituted 2-trifluroropyrroles under mild conditions and in moderate to good yields is reported. A number of alkoxysubstituted pyrroles were synthesized in yields which were lower than those of the amino-substituted pyrroles with N-dialkyl, N-dibenzyl, pyrrolidinyl, piperidinyl, and morpholine groups. The synthesis of the alkoxy-substituted acyclic precursors was reported earlier by the same group (A. Collar, G. Clar, M. A. P. Martins, S. Kimmer, P. Fischer Synthesis 1991, 483-486). Treatment with triphenylphosphine leads to the iminophosphoranes (Staudinger reaction), which then undergo an intramolecular aza-Wittig reaction to form the pyrroles.