Pramanik Sayan, Saha Pinaki, Ghosh Prasanta, Mukhopadhyay Chhanda
Department of Chemistry, University of Calcutta, 92 APC Road, Kolkata 700009, India.
Department of Chemistry, R. K. Mission Residential College, Narendrapur, Kolkata 700103, India.
ACS Omega. 2023 Jun 1;8(23):20579-20588. doi: 10.1021/acsomega.3c01046. eCollection 2023 Jun 13.
An operationally simple method for the synthesis of bridged dibenzo[b,f][1,5]diazocines and bridged spiromethanodibenzo[,]azepines exhibiting bridged eight-membered and seven-membered molecular architecture is reported. This unique approach is based on substrate selective mechanistic pathway, including an unprecendented aerial oxidation-driven mechanism for the synthesis of bridged spiromethanodibenzo[,]azepines. The reaction is highly atom economic, and in addition, it allows the construction of two rings and four bonds in a single operation under metal-free condition. The easy availability of β enaminone and ortho phathalaldehyde as starting materials and the simple operation make this approach suitable for the preparation of important dibenzo[b,f][1,5]diazocine and spiromethanodibenzo[,]azepine cores.
报道了一种操作简单的方法，用于合成具有桥连八元环和七元环分子结构的桥连二苯并[b,f][1,5]二氮杂环辛烷和桥连螺环甲氧基二苯并[,]氮杂卓。这种独特的方法基于底物选择性的反应机理，包括一种前所未有的空气氧化驱动的合成桥连螺环甲氧基二苯并[,]氮杂卓的机理。该反应具有高度的原子经济性，此外，它能够在无金属条件下通过一步反应构建两个环和四个化学键。β-烯胺酮和邻苯二甲醛作为起始原料易于获得，且操作简单，使得该方法适用于制备重要的二苯并[b,f][1,5]二氮杂环辛烷和螺环甲氧基二苯并[,]氮杂卓核心结构。
