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Reissert compound studies. XXXI. Emetine analogs based on the reaction of the reissert anion with 1,3,4,6,7,11b‐hexahydro‐9, 10‐dimethoxybenzo[ a ] quinolizin‐2‐ones
Author(s) -
Watts Raymond F.,
Popp Frank D.
Publication year - 1978
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.5570150805
Subject(s) - chemistry , emetine , cyanohydrin , medicinal chemistry , ion , stereochemistry , organic chemistry , catalysis , medicine , pharmacology
Reaction of the Reissert anion with the carbonyl group of 1,3,4,6,7,11b‐hexahydro‐9,10‐dimethoxybenzo[ a ]quinolizin‐2‐one and with 3‐ethyl‐1,2,3,4,6,7‐hexahydro‐9,10‐dimethoxy‐11b H ‐benzo[ a ]quinolizin‐2‐carboxaldehyde give emetine analogs. This anion does not react with the carbonyl group of 3‐aIkyl‐1,3,4,6,7,11b‐hexahydro‐9,10‐dimethoxybenzo[ a ]quinolizin‐2‐one but instead gives a rearrangement product and the benzoquinolizinone cyanohydrin.