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Transformations in the dibenzo[ a,d ]cycloheptene series
Author(s) -
Coppola Gary M.,
Hardtmann Goetz E.,
Koletar Gabor,
Kroin Stanley
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.5570180107
Subject(s) - chemistry , cycloheptene , raney nickel , hydrazide , hydrazine (antidepressant) , reagent , organic chemistry , hydrolysis , yield (engineering) , alkylation , curtius rearrangement , medicinal chemistry , acid hydrolysis , hydrogen , catalysis , materials science , chromatography , metallurgy
The synthesis of 5‐aminomethyl‐5‐hydroxy‐5 H ‐dibenzo[ a,d ]cycloheptene derivatives 3 was accomplished by two separate routes. The first route involves the reaction of 4 with Corey's Reagent followed by reaction with either amines or hydrazines. The reaction products with hydrazines ( e.g. 6 ) were hydrogenolyzed, either with hydrogen in the presence of platinum, or with hydrazine in the presence of Raney nickel to yield 3 . The second route to these compounds ( 3 ) proceeds by a Reformatsky reaction on 4 followed by acid‐hydrazide formation and Curtius degradation of 8 to afford spirooxazolidones 9 . Compounds 9 can be alkylated on nitrogen ( 10 ), and either 9 or 10 hydrolyzed to give the target compounds 3 .