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

JB Bremner, EJ Browne, PE Davies, LV Thuc

Index: Bremner; Browne; Davies; Le Van Thuc Australian Journal of Chemistry, 1980 , vol. 33, # 4 p. 833 - 841

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Citation Number: 10

Abstract

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 ...