National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad-500 037, India.
J Org Chem. 2011 Sep 2;76(17):7017-26. doi: 10.1021/jo200931m. Epub 2011 Aug 4.
An efficient one-pot reductive tandem mono-N-alkylation of both aromatic and aliphatic azides using dialkylboron triflates as alkylating agents has been examined under standardized reaction conditions. This methodology after optimization has been employed toward the syntheses of various secondary alkyl as well as aryl amines, including the synthesis of N10-butylated pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones via in situ azido reductive-cyclization process. This protocol is particularly attractive to provide an environmentally benign and practical method for mono-N-alkylation from organic azides without the use of toxic catalysts or corrosive alkylating agents. In addition, the mechanistic aspects have been investigated and the intermediates associated with this selective transformation have been intercepted and characterized by online monitoring of the reaction by ESI-MS/MS.
在标准化反应条件下，研究了用二烷基硼酸三氟甲磺酸酯作为烷基化试剂，高效一锅还原串联单 N-烷基化芳香族和脂肪族叠氮化物的方法。经过优化后，该方法已用于各种仲烷基和芳基胺的合成，包括通过原位叠氮还原环化过程合成 N10-丁基吡咯并[2,1-c][1,4]苯并二氮杂卓-5,11-二酮。该方案特别有吸引力，为有机叠氮化物的单 N-烷基化提供了一种环境友好且实用的方法，无需使用有毒催化剂或腐蚀性烷基化试剂。此外，还研究了反应的机理，通过 ESI-MS/MS 在线监测反应，截获并表征了与这种选择性转化相关的中间体。
