Metalation of Indole, N-Methylindole and N-Phenylindole with n-Butyllithium1a
Metalation of Indole, N-Methylindole and N-Phenylindole with n-Butyllithium1a
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吲哚、N-甲基吲哚和 N-苯基吲哚与正丁基锂的金属化1a
DOI：
10.1021/ja01098a035
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发表时间：
1953
影响因子：
15
通讯作者：
P. Roussel
中科院分区：
文献类型：
--
作者：
D. A. Shirley;P. Roussel
过量的正丁基锂作用于吲哚，然后用固体二氧化碳碳酸化，只得到n-吲哚羧酸，收率为61%。在各种实验条件下均未发现c -金属化的证据。n -甲基吲哚在2位金属化，产率78%。含有过量丁基锂的n -苯基吲哚通过分离出一种二羧酸（可能是1 -（2'-羧基苯基）-2-吲哚二羧酸）和一种可能来自同一种二硫硫化合物的环酮，显示出二金属化的证据。两种产物的二金属化收率均在55%左右。报道了一些利碘吲哚衍生物与多种试剂的反应产物。对吲哚及其某些衍生物与-丁基锂进行了金属化反应，以提供有关该有机金属化合物攻击位置的信息。正如过去所显示的，主要是由吉尔曼和他的同事，在杂离子中引入锂原子
Action of excess n-butyllithium on indole followed by carbonation with solid carbon dioxide gave only N-indolecarboxylic acid in 61% yield. There was no evidence of C-metalation under a variety of experimental conditions. N-Methylindole was metalated in the 2-position in 78% yield. N-Phenylindole with excess butyllithium showed evidence of dimetalation through the isolation of a dicarboxylic acid, probably l-(2'-carboxyphenyl)-2-indoIecarboxylic acid, and a cyclic ketone probably derived from the same dilithio compound. Both of the products represented a yield of dimetalation of about 55%. Reaction products of some of the lithioindole derivatives with a variety of reagents are reported.The metalation of indole and certain of its derivatives with «-butyllithium was undertaken to provide information concerning the position of attack by this organometalliccompound. As has been shown in the past, principally by Gilman and co-workers, introduction of a lithium atom into hetero-