114627-63-3Relevant academic research and scientific papers
Studies on Diazepines. XXIX. Syntheses of 3H- and 5H-1,4-Benzodiazepines from 3-Azidoquinolines
Sashida, Haruki,Fujii, Akira,Tsuchiya, Takashi
, p. 4110 - 4116 (2007/10/02)
Irradiation of the 3-azidoquinolines (6a-c) in the presence of sodium methoxide resulted in ring expansion to give the fully unsaturated 3-methoxy-3H-1,4-benzodiazepines (8).Further treatment of the 2-unsubstituted 3H-1,4-benzodiazepine (8a) with sodium methoxide in methanol gave the solvent adduct 7, which reverted to 8a on being refluxed in benzene, whereas the 2-substituted 3H-1,4-benzodiazepines (8b, c), upon treatment with sodium methoxide, underwent tautomerization to afford the 5H-1,4-benxodiazepines (15).Some reactions of the new 1,4-benzodiazepines (8 and 15) thus obtained were also examined.Keywords--3-azidoquinoline; 3H-1,4-benzodiazepine; 5H-1,4-benzodiazepine; photolysis; ring expansion; tautomerization; base treatment; quinolylnitrene
