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Syntheses Using the Michael Adddition of Phridinium Salts
Author(s) -
Kröhnke F.,
Zecher W.,
Curtze J.,
Drechsler D.,
Pfleghar K.,
Schnalke K. E.,
Weis W.
Publication year - 1962
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.196206261
Subject(s) - michael reaction , pyridinium , phenacyl , chemistry , adduct , organic chemistry , methylene , acceptor , catalysis , physics , condensed matter physics
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.