Author:
Bremner JB,Browne EJ,Davies PE,Thuc LV
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.
Cited by
17 articles.
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