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2005
Pyridine derivatives
R 0380
Efficient and Fast Heck Vinylation of 2-Bromo-6-methylpyridines with Methyl
Application to the Synthesis of 6-Methylcyclopenta[b]pyridinone. —
36- 128 Acrylate.
Heck vinylation of a variety of 2-bromopyridine derivatives (I) and (IV) is smoothly
achieved in the system NaOAc—Pd2Cl2(allyl)2/P(o-tolyl)3 in the presence of DMA.
Electronic and steric effects are studied. Best results are achieved in the presence of
6-substituents as well as complexing 3-substituents which prevent the complex formation of the pyridine nitrogen with the catalyst. The synthetic utility of this method is
demonstrated in the transformation of vinylpyridine derivative (IIIa) to cyclopentapyridone (VII), a precursor of 8-azasteroid analogues. — (ROBERT, N.; HOARAU, C.;
CELANIRE, S.; RIBEREAU, P.; GODARD, A.; QUEGUINER, G.; MARSAIS*, F.;
Tetrahedron 61 (2005) 19, 4569-4576; Lab. Chim. Org. Fine Heterocycl., IRCOF, Inst.
Natl. Sci. Appl. Rouen, F-76131 Mont-Saint-Aignan, Fr.; Eng.) — Mischke
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