An unexpected reaction of pyridine with acetyl chloride to give dihydropyridine and piperidine derivatives (Articolo in rivista)

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  • An unexpected reaction of pyridine with acetyl chloride to give dihydropyridine and piperidine derivatives (Articolo in rivista) (literal)
Anno
  • 2014-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1016/j.tetlet.2014.02.006 (literal)
Alternative label
  • Spanu P.; Mannu A.; Ulgheri F. (2014)
    An unexpected reaction of pyridine with acetyl chloride to give dihydropyridine and piperidine derivatives
    in Tetrahedron letters
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Spanu P.; Mannu A.; Ulgheri F. (literal)
Pagina inizio
  • 1939 (literal)
Pagina fine
  • 1942 (literal)
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  • http://www.scopus.com/inward/record.url?eid=2-s2.0-84897921750&partnerID=q2rCbXpz (literal)
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  • 55 (literal)
Rivista
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  • 11 (literal)
Note
  • Scopu (literal)
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  • Istituto di Chimica Biomolecolare - Consiglio Nazionale Delle Ricerche, Trav. La Crucca N 3, 07100 Sassari, Italy (literal)
Titolo
  • An unexpected reaction of pyridine with acetyl chloride to give dihydropyridine and piperidine derivatives (literal)
Abstract
  • An unexpected reaction of pyridine with acetyl chloride to give N-acetyl-1,2 and 1,4-dihydropyridyl acetic acid (1, 2) in high yield and regioselectivity has been reported. The key step is the formation of a zwitterionic pyridinium ketene enolate. The effect of different activating agents on the reaction yield and selectivity has been studied. Platinum(IV) mediated hydrogenation of the corresponding methyl esters (7, 8) gave piperidine derivatives (9, 10). © 2014 Elsevier Ltd. All rights reserved. (literal)
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