Reactions of fluoroalkyl-containing lithium 1,3-diketonates with diaminoarenes and 2-aminobenzenethiol |
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Authors: | V I Filyakova N S Boltacheva D V Sevenard V N Charushina |
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Institution: | 1.I. Ya. Postovsky Institute of Organic Synthesis,Ural Branch of the Russian Academy of Sciences,Ekaterinburg,Russian Federation;2.BITZ,Hansa Fine Chemicals GmbH,Bremen,Germany |
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Abstract: | 1,5-Benzob]- and 1,5-naphtho2,3-b]diazepines were synthesized by the reaction of lithium 1,3-diketonates with 1,2-diaminobenzene and 2,3-diaminonaphthalene
in an MeOH-AcOH-HCl mixture at 0 °C. The reactions of fluoroalkyl-containing lithium 1,3-diketonates with 1,2-diaminobenzene
and 1,2-diamino-4,5-difluorobenzene under reflux in acetic acid afford 2-fluoroalkyl-containing benzimidazoles as the major
products, whereas the reaction with 2-aminothiophenol gives 2-phenylbenzothiazole. The reactions of lithium diketonate containing
the cyclohexane and cyclopentane moieties with 1,2-diaminoarenes and 2-aminobenzenethiol are accompanied by the opening of
the carbocycle to form 2-(6-oxo-7,7,7-trifluoroheptyl)benzimidazole and 2-(5-oxo-6,6,6-trifluorohexyl)benzothiazole hydrates,
respectively. |
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