Solvent-free Heck-Jeffery reactions under ball-milling conditions applied to the synthesis of unnatural amino acids precursors and Indoles
Solvent-free Heck-Jeffery reactions under ball-milling conditions applied to the synthesis of unnatural amino acids precursors and Indoles
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DOI：
10.1055/s-2006-926371
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发表时间：
2006-04-04
影响因子：
2.6
通讯作者：
Frejd, T
中科院分区：
文献类型：
--
作者：
Tullberg, E;Schacher, F;Frejd, T
本文介绍了在球磨机中用Heck-Jeffery方法在无溶剂条件下合成了各种氨基和羟基取代的脱氢苯丙氨酸衍生物。讨论了吸电子基团和杂原子取代基相对于卤化物的位置的影响。适当取代的邻氨基脱氢苯丙氨酸衍生物与相应的2-取代吲哚发生环化消除反应。
The syntheses of various amino- and hydroxy-substituted dehydrophenylalanine derivatives using the Heck-Jeffery protocol under non-solvent conditions in a ball mill are presented. The influences of electron-withdrawing groups and of the location of the heteroatom substituent relative to the halide are discussed. Suitably substituted ortho-amino dehydrophenylalanine derivatives undergo a cyclization-elimination reaction to the corresponding 2-substituted indoles.