Syntheses Using the Michael Adddition of Phridinium Salts

Abstract

Abstract 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.