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The chemistry of cyclic enaminoketones. III. Synthesis of bi‐ and tricyclic enaminoketones from enamine esters and nitriles
Author(s) -
Meyers A. I.,
Reine A. H.,
Sircar J. C.,
Rao K. B.,
Singh S.,
Weidmann H.,
Fitzpatrick M.
Publication year - 1968
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570050201
Subject(s) - chemistry , enamine , tricyclic , benzene , toluene , scope (computer science) , organic chemistry , medicinal chemistry , catalysis , computer science , programming language
The cyclization of enamines derived from β‐aminoesters and β‐aminonitriles into bi‐ and tricyclic enaminoketones ( 6,9,13 and 24 ) has been investigated. The enamines derived from aminonitriles cyclize smoothly with magnesium perchlorate in benzene or toluene, whereas the enamines derived from aminoesters cyclize spontaneously during their formation. The scope and limitation of this process is discussed.