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Synthesis 2000; 2000(11): 1585-1590
DOI: 10.1055/s-2000-7618
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A Novel Facile Synthesis of 2,5-Di- and 2,3,5-Trisubstituted Pyrroles

Boris A. Trofimov* , Ol'ga A. Tarasova, Al'bina I. Mikhaleva, Nina A. Kalinina, Lidiya M. Sinegovskaya, Jochem Henkelmann
  • *A. E. Favorsky Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1, Favorsky Street, Irkutsk 664033, Russia; Fax + (7 39 52) 39 60 46; E-mail: bat@irioch.irk.ru
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Publication Date:
31 December 2000 (online)

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Heterocyclization of ketoximes with propyne or allene in superbase systems MOR/DMSO (M = K, Cs; R = H, t-Bu), which leads to 2-alkyl(aryl, hetaryl)-5-methyl- and 2,3-dialkyl-5-methylpyrroles or 2-methyl-4,5,6,7-tetrahydroindole in yields of up to 63%, has been accomplished for the first time. The reaction is mostly regioselective affording mainly or exclusively 2,5-di- and 2,3,5-trisubstituted pyrroles. The minor isomers in most cases are the corresponding 2,4-di and 2,3,4-trisubstituted pyrroles, only in the case of acetoxime the isomer ratio is ca 1 : 1. For oximes of methyl isopropyl ketone and pinacolone, the 4-methyl-isomers become predominant (78, 83%, respectively).

pyrroles - ketoximes - superbase systems - propyne - allene - heterocycles - regioselectivity