通过2-亚硝基苯甲腈的串联亚硝基-烯反应/分子内环化反应合成1-取代苯并[c]异恶唑-3(1H)-亚胺。
Synthesis of 1-substituted benzo[c]isoxazol-3(1H)-imines via tandem nitroso-ene/intramolecular cyclizations of 2-nitrosobenzonitrile.
作者信息
Jeffrey Jenna L, McClintock Sean P, Haley Michael M
机构信息
Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA.
出版信息
J Org Chem. 2008 Apr 18;73(8):3288-91. doi: 10.1021/jo800055e. Epub 2008 Mar 22.
PMID:18358045
Abstract
Instead of reacting via the expected coarctate cyclization pathway, 2-nitrosobenzonitrile undergoes a tandem nitroso-ene/intramolecular cyclization to form benzo[c]isoxazol-3(1H)-imines in very good yields under neutral conditions and at moderate temperatures. Treatment of three of the imines with HBF4 results in dimerization/condensation to furnish unusual, delocalized cationic systems.
摘要
2-亚硝基苯甲腈没有通过预期的缩环环化途径进行反应，而是经历了串联的亚硝基-烯/分子内环化反应，在中性条件和适中温度下以非常高的产率生成苯并[c]异恶唑-3(1H)-亚胺。用HBF4处理其中三种亚胺会导致二聚化/缩合反应，从而形成不寻常的离域阳离子体系。
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