Dipartimento di Scienze e Innovazione Tecnologica, Università del Piemonte Orientale A. Avogadro, Viale T. Michel 11, 15121 Alessandria, Italy.
Org Lett. 2012 Feb 3;14(3):716-9. doi: 10.1021/ol203101s. Epub 2012 Jan 19.
N,N'-Dibenzyl-6-hydroxymethyl-6-nitroperhydro-1,4-diazepine was converted into a nitronate via retro-Henry reaction, followed by either Michael reaction with several acrylic derivatives or Mannich reaction with different amines, thus leading to 6-substituted 6-nitroperhydro-1,4-diazepines. The tandem retro-Henry/Mannich reaction was also carried out using benzylamine as base, solvent, and reagent at the same time. Selective hydrogenation of the nitro group and complete hydrogenolysis were also successfully achieved.
N,N'-二苄基-6-羟甲基-6-硝基全氢-1,4-二氮杂环庚烷通过反 Henry 反应转化为硝𬭩盐，然后与几种丙烯衍生物进行迈克尔加成反应或与不同的胺进行Mannich 反应，从而得到 6-取代的 6-硝基全氢-1,4-二氮杂环庚烷。同时使用苄胺作为碱、溶剂和试剂进行串联反 Henry/Mannich 反应。还成功实现了硝基的选择性加氢和完全氢解。
