Syntheses Using the Michael Adddition of Phridinium Salts
Syntheses Using the Michael Adddition of Phridinium Salts
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DOI：
10.1002/anie.196206261
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发表时间：
1962-12
影响因子：
--
通讯作者：
F. Kröhnke;W. Zecher;J. Curtze;D. Drechsler;K. Pfleghar;K. Schnalke;W. Weis
中科院分区：
文献类型：
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作者：
F. Kröhnke;W. Zecher;J. Curtze;D. Drechsler;K. Pfleghar;K. Schnalke;W. Weis
通过将吡啶盐中的活性亚甲基Michael加成到合适的受体化合物上，可以通过简单的方法和一般良好的产率制备α-吡啶酮、取代吡啶，特别是吡啶羧酸和吡啶基吡啶，包括烟草烟碱的次要生物碱和缩合吡啶。由迈克尔加成物，可以制备多环芳烃，例如取代的荧蒽和“双荧蒽”;内部迈克尔加成导致吡咯啉并吡啶鎓盐。例如，吡啶鎓盐在醌上的迈克尔加成得到苯甲酰甲基取代的醌，由此可以容易地获得苯并呋喃和噌啉。
By Michael addition of the active methylene groups in pyridinium salts onto suitable acceptor compounds, α-pyridones, substituted pyridines, particularly pyridinecarboxylic acids and pyridylpyridines, including the minor alkaloid of tobacco nicotelline and annelized pyridines, can be prepared by a simple procedure and generally in good yields. From the Michael adducts, polycyclic aromatic hydrocarbons, e.g. substituted fluoranthenes and “bisfluoranthenes” can be prepared; internal Michael addition leads to pyrrolinopyrdinium salts. For example, Michael addition of pyridinium salts onto quinones gives phenacyl substituted quinones, from which benzofurans and cinnolines can be readily obtained.