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Synthesis of Benzo[ a ]quinolizidines via an Aza‐Michael/Oxidative Mannich Process
Author(s) -
Jung Areum,
Min SunJoon
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900137
Subject(s) - chemistry , michael reaction , adduct , organic chemistry , mannich reaction , oxidative phosphorylation , catalysis , biochemistry
The synthesis of substituted benzo[ a ]quinolizidines via aza‐Michael addition of tetrahydroisoquinolines to alkyl vinyl ketones, followed by oxidative Mannich cyclization, is described. Various Michael adducts are easily prepared, and subsequent DDQ‐mediated oxidations stereoselectively afford the corresponding azacycles efficiently. Furthermore, the one‐pot aza‐Michael/oxidative Mannich process gave benzo[ a ]quinolizidines, thus providing a metal‐free and practical synthetic route to N‐heterocyclic building blocks.