Reddy Chada Raji, Panda Sujatarani A, Reddy Motatipally Damoder
Division of Natural Products Chemistry, CSIR-Indian Institute of Chemical Technology , Hyderabad 500607, India.
Org Lett. 2015 Feb 20;17(4):896-9. doi: 10.1021/ol503752k. Epub 2015 Jan 30.
Synthesis of substituted pyridines through a novel aza-annulation of 2-en-4-ynyl azides, derived from MBH-acetates of acetylenic aldehydes, is described. A variety of enynyl azides having aryl, heteroaryl, and alkyl groups on the alkyne functionality successfully participated in the Ag-mediated annulation reaction to provide the corresponding 3,6-disubstituted pyridines. I2-mediated cyclization was found to be controlled by the substituent on the alkyne functionality, which offered the 5-iodo-3,6-disubstituted pyridines from enynyl azides having an electron-rich substituent on the alkyne functionality.
描述了通过由炔醛的MBH-乙酸酯衍生的2-烯-4-炔基叠氮化物的新型氮杂环化反应合成取代吡啶的方法。各种在炔基官能团上具有芳基、杂芳基和烷基的烯炔基叠氮化物成功参与了银介导的环化反应，以提供相应的3,6-二取代吡啶。发现碘介导的环化反应受炔基官能团上取代基的控制，该取代基从在炔基官能团上具有富电子取代基的烯炔基叠氮化物中提供5-碘-3,6-二取代吡啶。
