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A photochemical synthesis of 11 H ‐benzo[ a ]carbazole
Author(s) -
Olsen Robert J.,
Cummings O. William
Publication year - 1981
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.5570180248
Subject(s) - chemistry , carbazole , dehydrogenation , photodissociation , chloranil , medicinal chemistry , hydrolysis , photochemistry , stereochemistry , organic chemistry , catalysis
11 H ‐Benzo[ a ]carbazole was prepared from 5‐acetamido‐1,2,3,4‐tetrahydronaphthalene in four steps. A Goldberg arylation followed by hydrolysis afforded N ‐phenyl‐1,2,3,4‐tetrahydro‐5‐naphthylarnine ( 3 ). Photolysis of 3 produced 1,2,3,4‐tetrahydro‐11 H ‐benzo[ a ]carbazole ( 4 ) which was converted to 11 H ‐benzo[ a ]‐carbazole by dehydrogenation with chloranil.