413 4 archive 4 disk0/00/00/04/13 2006-11-17 2008-07-18 09:43:25 2008-07-16 15:45:55 article show Bremmer JB Browne EJ Davies PE Thuc LV pub 250000 restricted meisenheimer reearrangement Melt pyrolysis of the cis-6,7-dimethoxy-2-methyl-1-phenyl-1,2,3,4- tetrahydroisoquinoline N-oxide (2b) afforded the Meisenheimer rearrangement product, 7,8-dimethoxy-3-methyl-1-phenyl-1,3,4,5- tetrahydro-2,3-benzoxazepine (5b), in good yield, as did pyrolysis of the corresponding trans-N-oxide (3b) (in a melt) or a mixture of (2b) and (3b) (melt or in solution). The synthesis of the 1-deuterated analogue, (5c), of (5b) is described, together with products derived from (5b) by cleavage of the N-O bond which were used to confirm its structure. Meisenheimer rearrangement of the N-oxides (10) and (11) of 6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline and 2-methyl-1-phenyl-1,2,3,4- tetrahydroisoquinoline gave the analogous 2,3-benzoxazepine derivatives (12) and (13), respectively. 1980 published Australian Journal of Chemistry 33 4 833-841 http://www.publish.csiro.au/nid/51/paper/CH9800833.htm UNSPECIFIED TRUE http://www.publish.csiro.au/nid/51/paper/CH9800833.htm 736 1 413 1 application/pdf en staffonly cc_utas

chem1.pdf

chem1.pdf 2145397 http://eprints.utas.edu.au/413/1/chem1.pdf