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首页> 外文期刊>Journal of the Chemical Society, Perkin Transactions 1 >Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates
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Reductive cleavage of N-substituted aromatic amides as tert-butyl acylcarbamates

机译：N-取代的芳族酰胺作为叔丁基酰基氨基甲酸酯的还原裂解

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摘要

Synthetic and spectroscopic details relating to a set of heteroaromatic N-benzyl carboxamides and in particular thencorresponding tert-butyl acylcarbamates are reported. These compounds were required to study the postulated effectnof various heterocycles (pyridine and pyrazine with and without condensed benzene rings) on the cleavage of acyl–Nnbonds by reduction. All compounds were initially characterized by cyclic voltammetry (CV) which indicated variousndegrees of facilitated reduction, reflecting a direct influence of the heterocyclic component. Selected acylcarbamatesnwere studied with respect to acyl–N bond cleavage by mild reducing agents, and selectively deacylated by activatednaluminium and sodium borohydride. Conversion to acylcarbamates followed by reduction might therefore be a mild,nefficient two-step procedure to effect cleavage of amides, allowing isolation of carbamates and with sodiumnborohydride also the corresponding alcohols.
机译：报道了与一组杂芳族N-苄基羧酰胺，特别是然后相应的叔丁基酰基氨基甲酸酯有关的合成和光谱学细节。需要这些化合物来研究各种杂环（具有和不具有稠合苯环的吡啶和吡嗪）对通过还原作用裂解酰基-Nnbond的假定影响。所有化合物最初都通过循环伏安法（CV）进行表征，该伏安法表明各种程度的促进还原，反映了杂环组分的直接影响。研究了选择的酰基氨基甲酸酯对轻度还原剂裂解酰基-N键的影响，并通过活化的铝和硼氢化钠选择性地将其脱酰基。因此，转化为酰基氨基甲酸酯然后还原可能是温和，有效的两步程序，可实现酰胺的裂解，从而分离氨基甲酸酯，并用硼氢化钠分离相应的醇。

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