creators_name: Bremmer, JB
creators_name: Browne, EJ
creators_name: Davies, PE
creators_name: Raston, CL
creators_id: 
creators_id: 
creators_id: p.e.davies@utas.edu.au
creators_id: 
type: article
datestamp: 2006-11-17
lastmod: 2008-07-18 09:43:24
metadata_visibility: show
title: The Meisenheimer rearrangement in heterocyclic synthesis. II. Synthesis and X-ray crystal structure of a tetrahydro-1H-2,3-benzoxazocine and preparation of a hexahydro-2,3-benzoxazonine
ispublished: pub
subjects: 250100
full_text_status: restricted
keywords: meisenheimer rearrangement
abstract: 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
date: 1980
date_type: published
publication: Australian Journal of Chemistry
volume: 33
number: 6
pagerange: 1323-13334
id_number: http://www.publish.csiro.au/nid/51/paper/CH9801323.htm
thesis_type: UNSPECIFIED
refereed: TRUE
official_url: http://www.publish.csiro.au/nid/51/paper/CH9801323.htm
citation: Bremmer, JB and Browne, EJ and Davies, PE and Raston, CL (1980) The Meisenheimer rearrangement in heterocyclic synthesis. II. Synthesis and X-ray crystal structure of a tetrahydro-1H-2,3-benzoxazocine and preparation of a hexahydro-2,3-benzoxazonine. Australian Journal of Chemistry, 33 (6). pp. 1323-13334.
document_url: http://eprints.utas.edu.au/412/1/chem2.pdf