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The synthesis of 8‐oxoberbines containing a heterocyclic D‐ring by enamide photocyclizations
Author(s) -
Lenz George R.
Publication year - 1979
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.5570160304
Subject(s) - chemistry , dehydrogenation , benzofuran , ring (chemistry) , coumarin , thiophene , bicyclic molecule , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The photocyclization of 2‐heteroyl‐1‐methyleneyl‐3,4‐dihydro‐6,7‐dimethoxyisoquinolines, where heteroyl = benzofuran, benzo[ b ]thiophene, coumarin and nicotinoyl, leads to the corresponding 8‐oxoberbines containing a heterocyclic D‐ring. Dehydrogenation can accompany photocyclization depending on the reaction conditions employed, or alternatively DDQ can be used to effect this dehydrogenation.