1,4-恶嗪酮前体在通过分子间串联环加成/环化逆转构建吡啶衍生物中的应用。
Application of 1,4-Oxazinone Precursors to the Construction of Pyridine Derivatives by Tandem Intermolecular Cycloaddition/Cycloreversion.
作者信息
Carrillo Vallejo Nicole A, Scheerer Jonathan R
机构信息
Department of Chemistry, The College of William & Mary, P.O. Box 8795, Williamsburg, Virginia 23187, United States.
出版信息
J Org Chem. 2021 Apr 16;86(8):5863-5869. doi: 10.1021/acs.joc.1c00288. Epub 2021 Apr 2.
Abstract
This study reveals a new method for the preparation of 1,4-oxazinone derivatives by Staudinger reductive cyclization of functionalized vinyl azide precursors. The resulting oxazinone derivatives prepared in this manner were intercepted with terminal alkyne substrates through an intermolecular cycloaddition/cycloreversion sequence to afford polysubstituted pyridine products. Alkyne substrates bearing propargyl oxygen substitution showed good regioselectivity in the cycloaddition operation selectively affording 2,4,6-substituted pyridines. Application of this chemistry to the synthesis of an ErbB4 receptor inhibitor is also described.
摘要
本研究揭示了一种通过官能化乙烯基叠氮前体的施陶丁格还原环化反应制备1,4-恶嗪酮衍生物的新方法。以这种方式制备的所得恶嗪酮衍生物通过分子间环加成/环反转序列与末端炔烃底物反应，得到多取代吡啶产物。带有炔丙基氧取代基的炔烃底物在环加成反应中表现出良好的区域选择性，选择性地得到2,4,6-取代吡啶。还描述了这种化学方法在合成ErbB4受体抑制剂中的应用。
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