creators_name: Bremmer, JB
creators_name: Browne, EJ
creators_name: Davies, PE
creators_name: Thuc, LV
type: article
datestamp: 2006-11-17
lastmod: 2008-07-18 09:43:25
metadata_visibility: show
title: The Meisenheimer rearrangement in heterocyclic synthesis. I. Synthesis of some tetrahydro-2,3-benzoxazepines
ispublished: pub
subjects: 250000
full_text_status: restricted
keywords: meisenheimer reearrangement
abstract: 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.
date: 1980
date_type: published
publication: Australian Journal of Chemistry
volume: 33
number: 4
pagerange: 833-841
id_number: http://www.publish.csiro.au/nid/51/paper/CH9800833.htm
thesis_type: UNSPECIFIED
refereed: TRUE
official_url: http://www.publish.csiro.au/nid/51/paper/CH9800833.htm
citation: Bremmer, JB and Browne, EJ and Davies, PE and Thuc, LV (1980) The Meisenheimer rearrangement in heterocyclic synthesis. I. Synthesis of some tetrahydro-2,3-benzoxazepines. Australian Journal of Chemistry, 33 (4). pp. 833-841.
document_url: http://eprints.utas.edu.au/413/1/chem1.pdf