T. Gerasimova, A. V. Konstantinova, N. I. Petrenko
Oct 1, 1989
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Journal
Journal of Fluorine Chemistry
Abstract
Abstract Dibenz [b,f][1,4] oxazepines exhibit a variety of biological activities most of them being on the central nervous system. An approach to their polyfluorinated analogues, based on the intramolecular dehydrofluorination of polyfluoro-o-hydroxybenzylidenanilines, is presented. The interaction of polyfluorodibenz [b,f][1,4]oxazepines ( 1 ) with nucleophiles results in the substitution of para-fluorine. LAH reduction of ( 1 ) leads to 10,11-dihydrodibenzoxazepines ( 2 ) which can be converted to derivatives of the type ( 3 ). Dibenzoxazepinones ( 4 ) is obtained from compounds ( 1 ) and further transformed by the POCl3 to 11-chlorodibenz [b,f][1,4] oxazepines ( 5 ). Compounds ( 2 , 5 ) have been used as intermediates in the syntheses of polyfluorinated analogues of such psychotropic agents as Sintamil, loxapine and others.