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Paper | Regular issue | Vol 53, No. 3, 2000, pp.629-636
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8801
A Novel Synthesis of 2,3-Dialkylpyridine Derivatives from Dialkyl-N-silylimines and 1,3-Diaryl-2-propen-1-one or (E)-1,1,1-Trifluoro-4-phenyl-3-buten-2-one

Marhaba Hojahmat, Takeo Konakahara,* and Sanae Tamura

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


A series of 2,3-dialkylpyridine derivatives (4a-h) have been prepared by the reaction of dialky-N-silylimines (1a-c) with 1,3-diaryl-2-propen-1-one (3a-c) or (E)-1,1,1-trifluoro-4-phenyl-3-buten-2-one (3d). Dialkyl-N-trimethylsilylimines (1a-c), generated from alkyl cyanides and MeLi or n-BuLi and trimethylchloro- silane, reacted with a slight excess amount of 1,3-diaryl-2-propen-1-one (3a-c) or (E)-1,1,1-trifluoro-4-phenyl-3-buten-2-one (3d) in the presence of LDA in dry tetrahydrofuran to afford the corresponding 2,3-dialkylpyridine derivatives (4a-h) in 62-86 % yields, respectively.