412 9 archive 4 disk0/00/00/04/12 2006-11-17 2008-07-18 09:43:24 2008-07-16 15:45:53 article show P.E.Davies@utas.edu.au Bremmer JB Browne EJ Davies PE p.e.davies@utas.edu.au Raston CL pub 250100 restricted meisenheimer rearrangement The heterocyclic derivatives, 8,9-dimethoxy-3-methyl-1-phenyl-3,4,5,6- tetrahydro-1H-2,3-benzoxazocine(3a) and 9,10-dimethoxy-3-methyl-1- phenyl-1,3,4,5,6,7-hexahydro-2,3-benzoxazonine (3b),examples of two new ring systems, have been prepared by Meisenheimer rearrangement of the corresponding 2-benzazepine and 2-benzazocine N-oxide derivatives (2a) and (2b). The Bischler-Napieralski-type cyclization reaction was used in the preparation of the tertiary amine precursors of these N-oxides reaction conditions for the cyclization were critical and phosphorus oxychloride in refluxing butanenitrile was found to give the best yields of the seven- or eight-membered cyclic imine intermediates. Reductive cleavage of the benzoxazocine derivative (3a) with zinc in acetic acid followed by N-methylation gave the expected product, [2-{3- (dimethylamino)propyl}-4,5-di-methoxyphenyl]phenylmethanol (12). The crystal and molecular structure of (3a) has been determined by X-ray crystallographic analysis 1980 published Australian Journal of Chemistry 33 6 1323-13334 http://www.publish.csiro.au/nid/51/paper/CH9801323.htm UNSPECIFIED TRUE http://www.publish.csiro.au/nid/51/paper/CH9801323.htm 735 2 412 1 application/pdf en staffonly cc_utas

chem2.pdf

chem2.pdf 2821765 http://eprints.utas.edu.au/412/1/chem2.pdf