Studies on the nucleophilic addition to 3, 5-disubstituted pyridinium salts

R Lavilla, T Gotsens, S Rodríguez, J Bosch

Index: Lavilla, Rodolfo; Gotsens, Teresa; Rodiguez, Sonia; Bosch, Joan Tetrahedron, 1992 , vol. 48, # 31 p. 6445 - 6454

Full Text: HTML

Citation Number: 14

Abstract

The reactivity of pyridinium salts 2 towards nucleophiles has been studied. The interaction with enolates derived from esters 1 gave only trace amounts of the expected compounds 3. Irreversible-type additions, however, allowed the preparation of indolyldihydropyridines 8 and 9 with high yields. Reaction of organometallic 10 with salt 2c, followed by acidic cyclization, afforded tetracycle 12.