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Synlett 2000; 2000(3): 391-393
DOI: 10.1055/s-2000-6532
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2,5-Dialkylfurans and Nitroalkanes as Source of 2,3,5-Trialkylpyrroles

Roberto Ballini* , Luciano Barboni, Giovanna Bosica, Marino Petrini
  • *Dipartimento di Scienze Chimiche dell'Università, Via S. Agostino 1, 62032 Camerino (MC), Italy; Fax +39-07 37-63 73 45; E-mail: ballini@camserv.unicam.it
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Publikationsdatum:
31. Dezember 2000 (online)

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The synthesis of 2,3,5-trialkylpyrroles can be easily achieved by conjugate addition of nitroalkanes to 2-alken-1,4-dione (prepared by oxidative cleavage of 2,5-dialkylfuran) in acetonitrile with DBU as base, followed by chemoselective hydrogenation (10% Pd/C as catalyst) of the C-C double bond of the enones obtained by the elimination of nitrous acid from the Michael adduct. The Paal-Knorr reaction, performed on a bed of basic alumina and in the absence of a solvent, completes the formation of the title compounds.

2,5-dialkylfuran - nitroalkanes - pyrroles - Paal-Knorr reaction - basic alumina