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Synfacts 2008(2): 0130-0130
DOI: 10.1055/s-2007-992460
DOI: 10.1055/s-2007-992460
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Pyridine Ring Heterannulation via Imine-eneyne Ring Closure
S. R. Dubbaka, M. Kienle, H. Mayr, P. Knochel*
Ludwig-Maximilians-Universität München, Germany
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. Januar 2008 (online)
Significance
Reported is a synthesis of ring-annulated pyridines from iodine-induced cyclization of azadienyne intermediates. The lithio enyne, generated by metal-halogen exchange or deprotonation with t-BuLi, undergoes reaction with p-TolCN to give the conjugated imine which, by treatment with iodine undergoes an overall 6-endo-dig ring closure to give the substituted pyridine. The eneynic systems may be obtained through the use of a copper alkyne coupling methodology as shown.