通过多环芳基亚甲胺叶立德与腈的1,3-偶极环加成反应合成π-扩展咪唑。
Synthesis of π-Extended Imidazoles by 1,3-Dipolar Cycloaddition of Polycyclic Aromatic Azomethine Ylides with Nitriles.
作者信息
Li Qiang-Qiang, Ochiai Kotaro, Lee Cherie-Anne, Ito Shingo
机构信息
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore.
出版信息
Org Lett. 2020 Aug 7;22(15):6132-6137. doi: 10.1021/acs.orglett.0c02203. Epub 2020 Jul 14.
Here we report the 1,3-dipolar cycloaddition of polycyclic aromatic azomethine ylides with nitriles to produce highly fused imidazole derivatives, that is, tribenzo[,,]imidazo[2,1,5-]quinolizine. The advantages of this transformation are the broad substrate scope and the good functional group compatibility. The subsequent palladium-catalyzed intramolecular cyclization provides an efficient approach to further π-extended imidazoles, that is, 14b,15-diazadibenzo[,]cyclopenta[]pentaphene.
在此，我们报道了多环芳族甲亚胺叶立德与腈的1,3-偶极环加成反应，以生成高度稠合的咪唑衍生物，即三苯并[,,]咪唑并[2,1,5-]喹嗪。这种转化的优点是底物范围广且官能团兼容性好。随后的钯催化分子内环化反应为进一步的π-扩展咪唑，即14b,15-二氮杂二苯并[,]环戊并[]戊芬，提供了一种有效的方法。
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