- Chain-modified pyridino-N substituted nicotine compounds for use in the treatment of CNS pathologies
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Compounds for treating abuse of nicotinic receptor agonists, addiction to psychostimulant drugs, addiction to opiates, addiction to alcohol, addiction to tobacco products, addiction to nicotine, schizophrenia and related diseases, depression and related conditions, Alzheimer's disease, Parkinson's disease, irritable bowel syndrome, and colitis. The compounds competitively inhibit central nervous system acting nicotinic receptor agonists and act at the putative α3β2* and α4β2 neuronal nicotinic receptors in the central nervous system.
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Page column 6
(2010/02/05)
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- Total synthesis of gibbilimbols A-D
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Gibbilimbols A-D (1-4) were synthesized in 32-49% yield over four steps from commercially available starting materials. A copper-catalyzed coupling of 4-methoxyphenylmagnesium bromide with various unsaturated alkyl bromides was the key step in assembling the (long-chain alkyl)-phenol skeleton.
- Vyvyan, James R.,Holst, Christian L.,Johnson, Allison J.,Schwenk, Cheryl M.
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p. 2263 - 2265
(2007/10/03)
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- Regiospecific Nucleophilic Substitution in Cyclopropylcarbinols. Stereospecific Opening of the Cyclopropane Ring
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Reactions of cyclopropylcarbinols with hydrobromic acid and the triphenylphosphine-tetrabromomethane complex at 0°C result in stereospecific opening of the cyclopropane ring with formation of trans-homoallyl bromides.
- Matveeva,Kvasha,Kurts
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- SIMPLE SYNTHESIS OF ACETOGENIN TRANSOID INSECT PHEROMONES STARTING FROM ACETYLCYCLOPROPANE
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A highly effective synthesis of a series of alkyl and 1-alkenyl cyclopropyl ketones, which are key components in the complete synthesis of a large number of transoid lepidoptera pheromones, has been developed, based on the alkylation of N-cyclohexyl-1-cyclopropylethylideneimine or its condensation with aldehydes.
- Cheskis, B. A.,Ivanova, N. M.,Moiseenkov, A. M.,Nefedov, O. M.
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p. 1372 - 1380
(2007/10/02)
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- PHEROMONES OF INSECTS AND THEIR ANALOGS XXXIII. SYNTHESIS OF HEXADEC-7Z,11E-DIEN-1-YL ACETATE - THE SEX PHEROMONE OF Sitotroga cerealella AND A COMPONENT OF THE SEX PHEROMONE OF Pectinophora gossypiella
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From cyclohexene and caproaldehyde, using ozonolysis and the Knoevenagel reaction, we have synthesized hexadeca-7Z,11E-dien-1-yl acetate - the sex pheromone of Sitotroga cerealella and a component of the sex pheromone of Pectinophora gossypiella.
- Odinokov, V. N.,Ishmuratov, G. Yu.,Ladenkova, I. M.,Botsman, L. P.,Kargapol'tseva, T. A.,Tolstikov, G. A.
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p. 621 - 623
(2007/10/02)
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- Acetylcyclopropane as a Five-Carbon Building Block in the Synthesis of some Acetogenin Insect Pheromones
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Interaction of deprotonated acetylcyclopropane cyclohexylimine with several aliphatic alkyl halides, epoxides, and aldehydes efficiently gave the corresponding cyclopropyl ketones.Some of the respectible alcohols were rearranged in a highly stereoselective manner under the action of trimethylsilyl bromide in the presence of zinc bromide into the corresponding linear (E)-homoallyl bromides.The latter were used, in turn, as key intermediates in concise syntheses of thirteen terminally functionalized straight-chain oligoolefins which are known to constitute acetogenin pheromonal components for more than 65 species of lepidopteran insects.
- Moiseenkov, Alexander M.,Czeskis, Boris A.,Ivanova, Natalya M.,Nefedov, Oleg M.
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p. 2639 - 2649
(2007/10/02)
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- SIMPLE SYNTHESIS OF &β-SILYLOXYACYLCYCLOPROPANES AND THE HOMOALLYL REARRANGEMENT OF CYCLOPROPYLCARBINOLS BY THE ACTION OF TRIMETHYLSILYL HALIDES IN THE PRESENCE OF ZINC HALIDES
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The ZnCl2 catalyzed condensation of 1-trimethylsilyloxyvinylcyclopropane with aldehydes and ketones gave β-silyloxyacylcyclopropanes, which were converted by the action of TsOH in boiling benzene into 1-cyclopropyl-2E-alken-1-ones.Reduction of the latter gave saturated and allyl cyclopropylcarbinols, which by means of Me3SiX and catalytic amounts of ZnX2 (X = Cl, Br) were highly selectively converted into the corresponding linear mono- and dienic E-homoallyl halides.The sequence of reactions that was worked out provided an effective synthesis of 3E-dodecenyl acetate, a sex pheromone of the sugar beet moth.
- Cheskis, B. A.,Ivanova, N. M.,Moiseenkov, A. M.,Nefedov, O. M.
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p. 1839 - 1849
(2007/10/02)
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- Syntheses of Monounsaturated Sex Pheromones of Lepidoptera via 3-Alkyn-1-ols
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3-Alkyn-1-ols as intermediate synthons in the preparation of some Lepidoteran sex pheromones were utilized.Characteristic fragmentations reflecting the position of the triple bond were found in the mass spectra of 3-alkyn-1-ols and alkyn-1-yl acetates in contrast to 1-tert-butoxy-alkynes.A partial isomerization of 1-tosyloxy-3-(Z)-octene to 1-bromo-3-(E)-octene within the reaction with NaBr in DMF was noticed by GC and 13C-n.m.r., for which a mechanism involving homoconjugation in an intermediate non-classical carbonium ion was suggested.
- Pop, Lidia,Oprean, I.,Barabas, A.,Hodosan, F.
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p. 867 - 878
(2007/10/02)
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- REACTION DU TRIMETHYL CHLOROSILANE AVEC LES ALCOOLS α-CYCLOPROPANIQUES EN PRESENCE OU EN L'ABSENCE D'HALOGENURES DE LITHIUM.
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α-Cyclopropyl alcohols react with Me3SiCl, eventually in the presence of LiBr or LiI, leading to a cyclopropyl halide or (and) to a homopropargylic halide, according to the nature of the alcohol.
- Balme, Genevieve,Fournet, Guy,Gore, Jacques
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p. 1907 - 1908
(2007/10/02)
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- Regioselective Route to Sterically Hindered Cyclopropylcarbinyl Halides
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Reaction of cyclopropylcarbinyl alcohols 1 with hexachloroacetone and triphenylphosphine resulted in 80 - 90 percent yields of the corresponding cyclopropylcarbinyl chlorides 4 regioselectively, with no trace of the homoallylic chloride 2 or the chlorocyclobutane derivative 6a.Similar reaction of 1 with bromine and triphenylphosphine, in dimethylformamide, gave 65 - 80 percent yields of the cyclopropylcarbinyl bromide 5 with trace amounts of the homoallylic bromide 3 but no detectable bromocyclobutane derivative 6b.These reactions are amenable to the preparation of very sterically hindered cyclopropylcarbonyl halides, heretofore inaccessible, regioselectively and in a facile manner.
- Hrubiec, Robert T.,Smith, Michael B.
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p. 431 - 435
(2007/10/02)
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