Preparation and Study of Tautomers Derived from 2-(2'-Pyridyl) indole and Related Compounds

F Wu, J Hardesty, RP Thummel

Index: Wu, Feiyue; Hardesty, Jon; Thummel, Randolph P. Journal of Organic Chemistry, 1998 , vol. 63, # 12 p. 4055 - 4061

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Citation Number: 21

Abstract

Methylation of 2-(2'-pyridyl) indole provides the corresponding N-methylated salt that undergoes deprotonation with mild base to provide the tautomeric (E)-1-methyl-2-(2'- indolenylidene)-1, 2-dihydropyridine, whose geometry is established through a NOE experiment. Bridging at the 3, 3'-positions leads to tautomers having the opposite stereochemistry. A benzo-fused analogue exhibits similar behavior as does 2-(2'- ...