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Novel polycyclic heterocycles. XII. Reactions of 1,2‐dihydro‐11‐(trifluoromethyl)‐3 H ‐7 H ‐quino[8, 1‐ cd ] [1,5]‐benzoxazepin‐3‐one with aromatic aldehydes
Author(s) -
Yale Harry L.,
Petigara Ramesh B.
Publication year - 1974
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.5570110409
Subject(s) - chemistry , reagent , sodium hydroxide , trifluoromethyl , claisen condensation , condensation , medicinal chemistry , catalysis , condensation reaction , organic chemistry , alkyl , physics , thermodynamics
The Claisen‐Schmidt condensation between 1,2‐dihydro‐11‐(trifluoromethyl)‐3 H ,7 H ‐quino‐[8,1 ‐ cd ][1,5]benzoxazepin‐3‐one, 1 , and aromatic aldehydes has been investigated. The acid catalyzed reactions yielded the trans ‐2‐benzylidene derivatives, 4 ; the structures and configurations of the group of compounds represented by 4 have been confirmed by pmr in conjunction with the Eu(fod) 3 shift reagent. In contrast, catalysis with sodium hydroxide gave the isomeric 2‐benzyl‐ endo cyclic α,β‐unsaturated ketones, 3. Finally, the 4 could be isomerized to the corresponding 3 by means of sodium hydroxide. The ir, uv, and pmr spectra of these compounds are discussed.