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The synthesis of syn ‐ and anti ‐11‐hydroxy‐12‐methyl‐10,11‐dihydro‐5,10‐imino[5H] dibenzo[a,d] cycloheptene
Author(s) -
Dygos John H.
Publication year - 1976
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.5570130646
Subject(s) - chemistry , cycloheptene , solvolysis , derivative (finance) , stereochemistry , heptene , amine gas treating , medicinal chemistry , organic chemistry , bicyclic molecule , financial economics , hydrolysis , economics
The synthesis of anli ‐11 ‐hydroxy‐l 2‐methyl‐10,l 1 ‐dihydro‐5,10‐imino[5 H ]dibenzo[ a,d ]cyclo‐heptene ( 3 ) is reported. The assigned structure of 3 , was confirmed by comparison of the infrared and nmr spectra of 3 with that of the syn ‐1 1 ‐hydroxy derivative, 8 , prepared from 3 via a series of transformations. Key features in the synthesis include cyclization of an unsaturated amine to an azatetracyclic halide and solvolysis via an aziridinium ion to give 3.