134391-73-4Relevant academic research and scientific papers
Preparation of Didehydropyridines from (Trimethylsilyl)pyridines
Effenberger, Franz,Daub, Wolfgang
, p. 2119 - 2125 (2007/10/02)
Halogen-substituted (trimethylsilyl)pyridines 2, 3, 5-7 and trifluoromethylsulfonyloxy-substituted (trimethylsilyl)pyridines 9b, 11b are obtained from 2- and 3-halopyridines 1, 4 or hydroxypyridines 8, 10, and 12.Reactions of the 3- and 2-(trimethylsilyl)pyridines 2, 9b and 11b with bases in the presence of furans 15 give only protodesilylation or hydrolysis products but no indication is found for the formation of a 2,3-didehydropyridine. 3-Bromo-4-(trimethylsilyl)pyridine (5a) reacts with KOCMe3 in the presence of furan (15a) to give a mixture of products from which the isoquinoline derivative 20 and the tert-butoxypyridines 23, 24 are formed by addition to 3,4-didehydropyridine.Under comparable conditions far higher yields of 3,4-didehydropyridines are obtained by treatment of the 3-halo-2,4-bis(trimethylsilyl)pyridines 7 with strong bases. Key Words: Didehydropyridines, synthesis of
