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Synthesis 1994; 1994(3): 287-290
DOI: 10.1055/s-1994-25461
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Synthesis of Methyl 3-Aryl-4-trifluoromethyl-1H-pyrrole-2-carboxylates

Piero La Porta* , Luigi Capuzzi, Franco Bettarini
  • *Isagro s.r.l., Ricerca Fitofarmaci, Via G. Fauser 4, I-28100 Novara, Italy
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Publication Date:
27 September 2002 (online)

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Thermal addition of methyl 1-tert-butylaziridine-2-carboxylate (1) to 1-aryl-3,3,3-trifluoro-1-propynes 3 followed by dehydrogenation of intermediate pyrrolines 4,5 afforded isomeric methyl 1-tert-butyl-3(4)-aryl-4(3)-trifluoromethyl-1H-pyrrole-2-carboxylates 7 and 8 in high yields. Dealkylation of some 3-aryl derivatives, e. g. 7b,c with trifluoromethanesulfonic acid, gave methyl 3-aryl-4-trifluoromethyl-1H-pyrrole-2-carboxylates 9b,c.