Chichibabin amination of 1, X-naphthyridines. Nuclear magnetic resonance studies on the. sigma. adducts of heterocyclic systems with nucleophiles

…, HC Van der Plas, B Van Veldhuizen

Index: Haak, Henk J. W. van den; Plas, Henk C. van der; Veldhuizen, Beb van Journal of Organic Chemistry, 1981 , vol. 46, # 10 p. 2134 - 2137

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Citation Number: 16

Abstract

In the amination of 1, X-naphthyridines with potassium amide in liquid ammonia at about-35 to-40 OC the initial adduct formation is charge controlled. Thus, at these temperatures the site with the lowest electron density is most susceptible for amide attack ((2-2 in 1, 5- naphthyridine, C-2 in 1, 6-naphthyridine, C-2 and C-8 in 1, 7-naphthyridine, and C-2 in l,% naphthyridine), as proven by NMR spectroscopy. When the temperature was raised to ...