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A novel Barton decarboxylation produces a 1,4-phenyl radical rearrangement domino reaction
Tetrahedron ( IF 2.1 ) Pub Date : 2018-05-19 , DOI: 10.1016/j.tet.2018.05.043
Alejandro Manchado , Mercedes García , Mateo M. Salgado , David Díez , Narciso M. Garrido

A novel 1,4-Phenyl radical rearrangement (1,4-PhRR) is described in a typical Barton decarboxylation procedure. While carrying out this reaction in presence of a N,N-disubstituted β-amino acid derivative, the decarboxyphenyl rearranged derivative is obtained, as well as in presence of β-N,N-acylamide. On the other hand, secondary amines give the β-lactam derivative without rearrangement, as well as N-Fmoc derivatives give the normal decarboxylation reaction. In regards of amines which are far away from the carboxylic group, such as δ-amino acid derivatives, the reaction occur through a typical Barton decarboxylation without rearrangement. The diversity of the reaction proves synthetic usefulness paving the way to interesting biologically active compounds.



中文翻译:

新的Barton脱羧反应产生1,4-苯基自由基重排多米诺反应

在典型的Barton脱羧程序中描述了一种新颖的1,4-苯基自由基重排(1,4-PhRR)。在NN-二取代的β-氨基酸衍生物的存在下进行该反应时,获得脱羧苯基重排的衍生物,以及在β - N,N-酰基酰胺的存在下。另一方面,仲胺产生β-内酰胺衍生物而没有重排,而N- Fmoc衍生物产生正常的脱羧反应。关于远离羧基的胺,例如δ-氨基酸衍生物,该反应通过典型的Barton脱羧而没有重排发生。反应的多样性证明了合成的有用性,为有趣的生物活性化合物铺平了道路。

更新日期:2018-05-19
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