- COMPOUNDS CAPABLE OF INHIBITING VOLTAGE GATED CALCIUM ION CHANNEL, AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
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Disclosed herein are an N-(pyrazolylmethyl)arylsulfonamide derivative useful as a calcium ion channel blocker, a pharmaceutically acceptable salt thereof, and the medicinal use thereof as a therapeutic agent using its calcium ion channel blocking effect.
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Paragraph 0154; 0155
(2015/12/12)
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- Mild N-deacylation of secondary amides by alkylation with organocerium reagents
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Secondary amides are a class of highly stable compounds serving as versatile starting materials, intermediates and directing groups (amido groups) in organic synthesis. The direct deacylation of secondary amides to release amines is an important transformation in organic synthesis. Here, we report a protocol for the deacylation of secondary amides and isolation of amines. The method is based on the activation of amides with Tf2O, followed by addition of organocerium reagents, and acidic work-up. The reaction proceeded under mild conditions and afforded the corresponding amines, isolated as their hydrochloride salts, in good yields. In combination with the C-H activation functionalization methodology, the method is applicable to the functionalization of aniline as well as conversion of carboxylic derivatives to functionalized ketones.
- Wang, Ai-E.,Chang, Zong,Liu, Yong-Peng,Huang, Pei-Qiang
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supporting information
p. 1055 - 1058
(2015/09/01)
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- Site-selective oxidation of unactivated C sp 3-H bonds with hypervalent iodine(III) reagents
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By design: The site-selective oxidation of unactivated secondary C sp 3-H bonds was accomplished with hypervalent iodine(III) reagents and tert-butyl hydroperoxide (see scheme). The preparation and derivatization of the hypervalent iodine(III) reagent are simple, thus allowing the rational design of these reagents to optimize the site selectivity of the oxidation. Copyright
- Moteki, Shin A.,Usui, Asuka,Zhang, Tiexin,Solorio Alvarado, Cesar R.,Maruoka, Keiji
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supporting information
p. 8657 - 8660
(2013/09/12)
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- α,β-Unsaturated imines via Ru-catalyzed coupling of allylic alcohols and amines
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A convenient synthesis of α,β-unsaturated imines requiring only an allylic alcohol, an amine and a Ru catalyst has been developed. The use of large excesses of oxidant and the purification of sensitive intermediates can be avoided.
- Rigoli, Jared W.,Moyer, Sara A.,Pearce, Simon D.,Schomaker, Jennifer M.
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supporting information; experimental part
p. 1746 - 1749
(2012/04/23)
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- Synthesis of 2-hydroxy-5-methyl-3-hexanone
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2-Hydroxy-5-methyl-3-hexanone, which is a characteristic component of eucalyptus honeys, was synthesised by oxidation of the silyl enol ether of 5-methyl-3-hexanone. 5-Methyl-3-hexanone was prepared by Grignard reaction and oxidation starting from isovaleraldehyde and ethylmagnesium bromide. The desired silyl enol ether was produced with high selectivity by deprotonation of 5-methyl-3-hexanone with NaHMDS in n-hexane followed by reaction with chlorotrimethylsilane and then oxidised by MCPBA to give pure 2-hydroxy-5-methyl-3-hexanone in about 77% yield after purification by flash chromatography. 2-Hydroxy-5-methyl-3-hexanone has a cheese and sour milk odour.
- Tian, Hong-Yu,Ye, Hong-Lin,Sun, Bao-Guo,Wang, Ya-Ling
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experimental part
p. 51 - 52
(2011/05/07)
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- Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution
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Full details of the kinetic resolution of tertiary nitroaldols derived from simple ketones are described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. Using
- Hara, Keiichi,Tosaki, Shin-ya,Gnanadesikan, Vijay,Morimoto, Hiroyuki,Harada, Shinji,Sugita, Mari,Yamagiwa, Noriyuki,Matsunaga, Shigeki,Shibasaki, Masakatsu
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scheme or table
p. 5030 - 5036
(2009/12/03)
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- Reduction of α,β-unsaturated ketones with diphenylsilanes bearing several substituents on their phenyl moiety catalyzed by rhodium-phosphine complexes
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1,4-Addition product was afforded exclusively by rhodiumphosphine complex-catalyzed hydrosilylation by using 2-cyclohexen-1-one and a dihydrosilane bearing an ether substituent in spite of the fact that dihydrosilanes were believed to give 1,2-addition product selectively. Copyright
- Imao, Daisuke,Hayama, Miyuki,Ishikawa, Kohta,Ohta, Tetsuo,Ito, Yoshihiko
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p. 366 - 367
(2007/10/03)
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- Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution
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A kinetic resolution of tertiary nitroaldols derived from simple ketones is described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. By using a mixture of La-Li3-(1a)3 complex (LLB 2a) and La-Li3-(1b)3 (LLB* 2b) complex in a ratio of 2/1, chiral tertiary nitroaldols were obtained in 80-97% ee and 30-47% recovery yield. Copyright
- Tosaki, Shin-Ya,Hara, Keiichi,Gnanadesikan, Vijay,Morimoto, Hiroyuki,Harada, Shinji,Sugita, Mari,Yamagiwa, Noriyuki,Matsunaga, Shigeki,Shibasaki, Masakatsu
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p. 11776 - 11777
(2007/10/03)
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- Facile deoxygenation of dicarbonyl compounds using a samarium diiodide-additive system
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The reduction of α- and β-dicarbonyl compounds was investigated with samarium diiodide in the presence of additive. Diketones and ketocarboxylic acids were easily reduced at room temperature to give the mono-alcohols in good to excellent yield, and ketoester afforded the saturated ester as the major product in moderate yield. These reductions containing the reductive deoxygenation can be rapidly performed under the facile and mild conditions by this method.
- Kamochi, Yasuko,Kudo, Tadahiro,Masuda, Toshinobu,Takadate, Akira
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p. 1017 - 1020
(2007/10/03)
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- Mammalian exocrine secretions XI. Constituents of the preorbital secretion of klipspringer, Oreotragus oreotragus
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The ketones 3-pentanone, 4-methyl-2-pentanone, 5-methyl-3-hexanone, 4-methyl-3-hexanone, and the esters ethyl propaneate, 2-methylpropyl acetate, ethyl 3-methylbutanoate, and 2-methylpropyl propanoate were identified as the only volatile organic constituents of the preorbital secretion of the klipspringer. Oreotragus oreotragus. These compounds are considerably more volatile than those found in the preorbital secretions of other antelopes belonging to the tribe Antelopini. More than 50% of the preorbital secretion consists of proteinaceous material, which probably acts as a controlled-release substance in retarding the evaporation of the volatile constituents of the secretion from territorial marks.
- Burger
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p. 2383 - 2400
(2007/10/03)
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- 3-Metallated enamines XI. Transmetallation of 3-Stannylated enamines - A new method to generate 1-aminoallyllithium compounds
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The transmetallation of 3-stannylated enamines, 1-morpholino-3-(trialkylstannyl)cycloalk-1-enes and 3-morpholino-5-(tributylstannyl)hex-3-ene, with butyllithium is a new and general way to generate s1-aminoallyllithium compounds. Stabilization by aromatic substituents is not further necessarily as in the case of preparation by deprotonation and even the thermodynamically less stable exoamino derivatives are accessible. Therefore homoenolate-equivalents of cyclic ketones are made available. Thus, the corresponding 3-alkylated or 3-silylated cycloalkanones and alken-3-ones were prepared via the 1-morpholinoallyllithium compounds.
- Ahlbrecht,Weber
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p. 1018 - 1025
(2007/10/02)
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- ADDITION RADICALAIRE DU PROPANAL A DIVERS ALCENES ET CYCLENES : ASPECTS STERIQUES ET POLAIRES
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Free radical addition of propanal to double bonds, initiated by benzoyl peroxide, mainly leads to two adducts, an aldehyde and a ketone, when the double bond has a methylene group ; these results are explained in terms of polar effects in the free radical transfert reactions.When the double bond has no methylene group, only the ketonic adduct is obtained ; the steric effects in the free radical addition step explain these results.
- Tabbaa, I.,Cazaux, M.,Lalande, R.
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p. 1011 - 1018
(2007/10/02)
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- A THREE COMPONENT KETONE SYNTHESIS FROM A PHENYLTHIOVINYLPHOSPHINE OXIDE
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The anion formed by addition of an alkyl-lithium to the vinyl phosphine oxide (4) reacts with aldehydes to give vinyl sulphides, easily hydrolysed to ketones.
- Warren, Stuart,Zaslona, Alex T.
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p. 4167 - 4170
(2007/10/02)
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- A NEW SYNTHESIS OF KETONES FROM 1,2-DIMETHOXYETHENYLLITHIUM, ORGANOBORANES, AND ALKYL FLUOROSULFONATES
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The reaction of alkyl fluorosulfonates with lithium 1,2-dimethoxyethenyltrialkylborates readily prepared from organoboranes gives corresponding ketones in good yields.
- Yogo, Toshinobu,Koshino, Junji,Suzuki, Akira
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p. 1059 - 1060
(2007/10/02)
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- Cp2TiCl2-CATALYZED GRIGNARD REACTIONS. 3. REACTIONS WITH ESTERS: EFFICIENT METHODOLOGY FOR THE SYNTHESIS OF SECONDARY ALCOHOLS AND FOR THE REDUCTION OF ESTERS TO PRIMARY ALCOHOLS
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Cp2TiCl2-catalyzed Grignard reactions with esters provide general methodology for preparation of secondary alcohols or for reduction of esters to the corresponding primary alcohols.
- Sato, Fumie,Jinbo, Takamasa,Sato, Masao
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p. 2175 - 2178
(2007/10/02)
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- Cardioglycoside derivatives of the strophanthidin type, a process for their manufacture and medicinal preparations containing these compounds
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Cyclic acetals or ketals of cardioglycosides derived from k-strophanthidin or strophanthidol are more readily absorbed by the stomach and intestine than the parent cardioglycoside. The acetals are produced by reaction of the parent cardioglycoside, e.g., strophanthidindigitoxide, with an aldehyde or ketone, or the corresponding acetal or ketal, in the presence of an acid condensation catalyst, to produce the k-strophanthidin derivative optionally followed by reduction to the strophanthidiol derivative.
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