The tautomeric structures of 5-hydroxycotinine, a secondary mammalian metabolite of nicotine

TL Nguyen, E Dagne, L Gruenke…

Index: Nguyen; Dagne; Gruenke; et al. Journal of Organic Chemistry, 1981 , vol. 46, # 4 p. 758 - 760

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Citation Number: 23

Abstract

A novel synthesis of 5-hydroxycotinine has provided a homogenous product which has been examined spectroscopically in order to assew the possible equilibrium of the hydroxy lactam with the tautomeric keto amide structure originally proposed for this urinary metabolite of the tobacco alkaloid nicotine. Treatment of the readily available (S)-3, 3-&bromocotinine with methanolic KOH led to (R~-l-methyl-5 (3'-pyridyl)-5methoxypyrrolin-2e which upon ...