Bulletin of the Chemical Society of Japan p. 1064 - 1073 (2015)
Update date:2022-09-26
Topics:
Okuma, Kentaro
Tanabe, Yukiko
Nagahora, Noriyoshi
Shioji, Kosei
2,3-Benzodiazepines were synthesized by two-step or one-pot reactions from aryne precursors. Reaction of 2- (trimethylsilyl)aryl triflates with β-diketones in the presence of CsF gave ortho-substituted benzophenones. Treatment of benzophenones with hydrazine hydrate resulted in the formation of 2,3-benzodiazepines in moderate yields. Tofisopam, a well known anxiolytic, could be synthesized via C-C bond insertion of 3,4-dimethoxybenzyne with 2-ethyl-1-(3,4-dimethoxyphenyl)butane-1,3-dione, followed by the reaction with hydrazine hydrate in one-pot operation. 2,3-Benzodiazepin-4-ones were also synthesized by the reaction of β-keto esters with triflates in the presence of CsF, followed by the addition of hydrazine hydrate. Substituted isoquinolines were synthesized by the reaction of ortho-substituted benzophenones with ammonium hydroxide.
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