首页> 外文期刊>The Journal of Organic Chemistry >Effcient synthesis of 1-amino-2-naphthalenecarboxylic acid derivatives via a sequential michael addition/enolate-nitrile coupling route and its application to facile preparation of 9-amino analogues of arylnaphthofuranone lignans
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Effcient synthesis of 1-amino-2-naphthalenecarboxylic acid derivatives via a sequential michael addition/enolate-nitrile coupling route and its application to facile preparation of 9-amino analogues of arylnaphthofuranone lignans

机译:通过连续的迈克尔加成/烯醇盐-腈偶联途径有效合成1-氨基-2-萘甲酸衍生物及其在轻松制备芳基萘呋喃酮木脂9-氨基类似物中的应用

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摘要

The reaction of 2-(α-lithioalkyl)benzonitriles, generated in situ by treatment of 2-alkylbenzonitriles with LDA in diglyme, with α,β-unsaturated carboxylates and nitriles produced 1-amino-3,4-dihydro- 2-naphthalenecarboxylates and carbonitriles in 54-98/100 yields through Michael addition of the lithio nitroles to α,β-unsaturated carboxylic acid derivatives, followed by zinc iodide-promoted intramolecular enolate-nitrile coupling of the resulting enolate intermediates.
机译:通过在二甘醇二甲醚中用LDA处理2-烷基苯甲腈就地生成的2-(α-硫代烷基)苯甲腈与α,β-不饱和羧酸盐和腈的反应生成了1-氨基-3,4-二氢-2-萘甲酸乙酯和甲腈以54-98 / 100的产率生成甲硫氨酸,方法是将硫代硫醇迈克尔加成到α,β-不饱和羧酸衍生物上,然后碘化锌促进分子内烯醇盐-腈偶联生成的烯醇盐中间体。

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