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The Meisenheimer rearrangement in heterocyclic synthesis. I. Synthesis of some tetrahydro-2,3-benzoxazepines


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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.

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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.

Item Type: Article
Keywords: meisenheimer reearrangement
Journal or Publication Title: Australian Journal of Chemistry
Page Range: pp. 833-841
Identification Number - DOI: http://www.publish.csiro.au/nid/51/paper/CH9800833.htm
Date Deposited: 17 Nov 2006
Last Modified: 18 Nov 2014 03:12
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