- ARYL-SUBSTITUTED PIPERAZINE DERIVATIVES
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Aryl-substituted piperazine derivatives are provided. Such compounds may be used to modulate MCH receptor activity in vivo or in vitro, and are particularly useful in the treatment of a variety of metabolic, feeding and sexual disorders in humans, domesti
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- 4-(1-HYDROPEROXY-1-METHYLETHYL)-1,3-CYCLOPENTADIENYL METHYL KETONE: ITS FORMATION FROM α-TERPINEOL AND BEHAVIOR AS A DIMETHYLFULVENE EPOXIDE.
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Ozonolysis of α-terpineol (1) then steam distillation in presence of acid gives the known 4-isopropylidenecyclopentenyl methyl ketone (4).This is oxidized in air to 4-(1-hydroperoxy-1-methylethyl)-1,3-cyclopentadienyl methyl ketone (10), a compound frequently reacting as if it were one of the elusive dimethylfulvene epoxides.It is converted by silica gel to two dimers (12, 13) of 2-acetyl-6,6-dimethylfulvene epoxide (19).Catalytic reduction of the dimers occurs mostly by exo addition of hydrogen to the conjugated double bond, and thermolysis of the dimers yields 4-acetyl-6,6-dimethylcyclohexa-2,4-dienone (20).With triphenylphosphine the hydroperoxide (10) yields two dimers of 2-acetyl-6,6-dimethylfulvene (26).This is the first reported isolation of dimers of a fulvene.The hydroperoxide (10) adds diazomethane to give an unstable pyrazoline (28); this pyrazoline loses nitrogen to yield a single isomer o' 5-acetyl-3',3'-dimethylbicyclohex-3-ene-2-spiro-2'-oxirane (29).Catalytic hydrogenation of the latter involves ring opening of the epoxide.
- Thomas, Alan F.,Perret, Celia
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p. 3311 - 3322
(2007/10/02)
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- PHENYLETHANOLAMINE DERIVATIVES, III. SYNTHESIS OF 1-(HYDROXY- AND METHOXYPHENYL)-2-AMINOETHANOL DERIVATIVES
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New 1-(methoxyphenyl)- and 1-(hydroxyphenyl)-2-aminoethanol derivatives have been prepared for the purpose of biological testing.The compounds were obtained via aminolysis of the corresponding phenacyl halides and subsequent reduction of the resulting phenacylamines with sodium tetrahydridoborate.In the aminolysis of phenacyl halides O-benzoyl-ω-hydroxyaminoacetophenones and 1,2-dibenzoylethanes were formed as by-products.In some cases the 4-methoxy-ω-aminoacetophenones were hydrolyzed by aqueous hydrogen bromide into the corresponding glycine and phenol.
- Hajoos, Andor
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