- Synthesis of 2,3-benzodiazepines and 2,3-benzodiazepin-4-ones from arynes and β-diketones
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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.
- Okuma, Kentaro,Tanabe, Yukiko,Nagahora, Noriyoshi,Shioji, Kosei
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p. 1064 - 1073
(2015/09/01)
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- One-pot synthesis of 2,3-benzodiazepines from arynes and β-diketones
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Novel one-pot synthesis of 2,3-benzodiazepines from aryne precursors was accomplished. Tofisopam, well-known anxiolytics, could be synthesized via C-C bond insertion of 4,5-dimethoxybenzyne with 2-ethyl-1-(3,4-dimethoxyphenyl)- butane-1,3-dione, followed by the reaction with hydrazine hydrate in a one-pot operation. This protocol is applicable to the synthesis of other biologically active 2,3-benzodiazepines, such as Girisopam and Nerisopam.
- Okuma, Kentaro,Tanabe, Yukiko,Itoyama, Ryoichi,Nagahora, Noriyoshi,Shioji, Kosei
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p. 1260 - 1262
(2013/10/22)
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- A simple and efficient synthesis of GYKI 52466 and GYKI 52895
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The synthesis of 1-(4-aminophenyl)-4-methyl-7,8-methylene-dioxy-5H-2,3-benzodiazepine (GYKI 52466, 1), the prototype of a series of noncompetitive AMPA receptor antagonists, and its 3,4-dihydroderivative (GYKI 52895, 2) is described. The title compounds have been prepared starting from safrole through a quite effective procedure.
- Zappala, Maria,Grasso, Silvana,Micale, Nicola,Polimeni, Santina,De Micheli, Carlo
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p. 527 - 533
(2007/10/03)
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