74904-70-4Relevant academic research and scientific papers
The Characterization and Thermolysis of cis- and trans-(+/-)-Laudanosine N-Oxide
Bremner, John B.,Thuc, Le van
, p. 379 - 394 (2007/10/02)
The isolation and characterization of cis- and trans-(+/-)-laudanosine N-oxide is described.Thermolysis of cis-(+/-)-laudanosine N-oxide afforded the new fused and bridged heterocyclic derivatives (3RS,3aRS,8aSR)-3-(3,4-dimethoxyphenyl)-5,6-dimethyoxy-1-methyl-3,3a,8,8a-tetrahydro-1H-indeno-isoxazole (18) and (1RS,2RS,4RS)-2-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydro-2H-1,4-methano-4H-3,4-benzoxazocine (19); other products included (+/-)-laudanosine, the Cope elimination product, (E)-N-2--4,5-dimethoxyphenyl>ethyl-N-methylhydroxyalamine (4) and 1-(3,4-dimethoxybenzyl)-7,8-dimethoxy-3-methyl -1,3,4,5-tetrahydro-2,3-benzoxazepine (17), the product of a Meisenheimer rearrangement.By contrast, trans-(+/-)-laudanosine N-oxide gave (4) in nearly quantitative yield.Some of the possible mechanistic implications of these results are discussed
