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Paper | Regular issue | Vol 45, No. 2, 1997, pp.271-276
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7634
Synthesis of 2,3,4,6-Tetra-substituted Pyridines from N-Silyl-1-aza-allyl Anions and 1,3-Diphenyl-2-propen-1-one

Takeo Konakahara,* Marhaba Hojahmat, and Kenji Sujimoto

*Department of Industrial Chemistry, Faculty of Science and Technology, Science University of Tokyo, 2641 Yamazaki, Noda, Chiba 278-8510, Japan


The reaction of N-silyl-1-aza-allyl anions (3) with 1,3-diphenyl-2-propen-1-one (4) is described. The anions (3a-f), which were prepared from an α-silyl carbanion of 3-methyl-5-trimethylsilylmethylisoxazole (1a) [or 2-trimethylsilylmethylpyridine (1b)] and p-substituted benzonitriles (2a-e, R1 = H, p-Me, p-OMe, p-Cl, p-CF3), reacted with a slightly excess amount of 1,3-diphenyl-2-propen-1-one (4) to afford 2,3,4,6-tetra-substituted pyridine derivatives (5a-f) in good yields. But the analogous reaction of the anion (3e) with cinnamaldehyde or methyl vinyl ketone did not give the corresponding pyridines.