Regioselective metalation of the 4-position of pyridine. New and convenient alkylation and acylation of 3-amino-5-methoxypyridine

Y Tamura, M Fujita, LC Chen, M Inoue…

Index: Tamura, Yasumitsu; Fujita, Masanobu; Chen, Ling-Ching; Inoue, Minako; Kita, Yasuyuki Journal of Organic Chemistry, 1981 , vol. 46, # 17 p. 3564 - 3567

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Citation Number: 29

Abstract

Prior to the work of Meyers' v2 using the oxazdine functionality as an activating group, the direct metalation of pyridine was limited to a few example^.^^^ The Meyers method gives a regioselective metalation of the 3-position of 4-(4, 4-dimethyloxazolinyl-2-yl) pyridine by methyllithium and the 4-position of 3-(4, 4-dimethyloxazolinyl-2-y1) pyridine by lithium amide. Very recently, regioselective lithiation of ethyl esters of nicotinic and isonicotinic ...