623-56-3Relevant academic research and scientific papers
Mild N-deacylation of secondary amides by alkylation with organocerium reagents
Wang, Ai-E.,Chang, Zong,Liu, Yong-Peng,Huang, Pei-Qiang
supporting information, p. 1055 - 1058 (2015/09/01)
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.
COMPOUNDS CAPABLE OF INHIBITING VOLTAGE GATED CALCIUM ION CHANNEL, AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
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Paragraph 0154; 0155, (2015/12/12)
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.
Site-selective oxidation of unactivated C sp 3-H bonds with hypervalent iodine(III) reagents
Moteki, Shin A.,Usui, Asuka,Zhang, Tiexin,Solorio Alvarado, Cesar R.,Maruoka, Keiji
supporting information, p. 8657 - 8660 (2013/09/12)
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
α,β-Unsaturated imines via Ru-catalyzed coupling of allylic alcohols and amines
Rigoli, Jared W.,Moyer, Sara A.,Pearce, Simon D.,Schomaker, Jennifer M.
supporting information; experimental part, p. 1746 - 1749 (2012/04/23)
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.
Synthesis of 2-hydroxy-5-methyl-3-hexanone
Tian, Hong-Yu,Ye, Hong-Lin,Sun, Bao-Guo,Wang, Ya-Ling
experimental part, p. 51 - 52 (2011/05/07)
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.
Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution
Hara, Keiichi,Tosaki, Shin-ya,Gnanadesikan, Vijay,Morimoto, Hiroyuki,Harada, Shinji,Sugita, Mari,Yamagiwa, Noriyuki,Matsunaga, Shigeki,Shibasaki, Masakatsu
scheme or table, p. 5030 - 5036 (2009/12/03)
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
Reduction of α,β-unsaturated ketones with diphenylsilanes bearing several substituents on their phenyl moiety catalyzed by rhodium-phosphine complexes
Imao, Daisuke,Hayama, Miyuki,Ishikawa, Kohta,Ohta, Tetsuo,Ito, Yoshihiko
, p. 366 - 367 (2007/10/03)
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
Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution
Tosaki, Shin-Ya,Hara, Keiichi,Gnanadesikan, Vijay,Morimoto, Hiroyuki,Harada, Shinji,Sugita, Mari,Yamagiwa, Noriyuki,Matsunaga, Shigeki,Shibasaki, Masakatsu
, p. 11776 - 11777 (2007/10/03)
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
Facile deoxygenation of dicarbonyl compounds using a samarium diiodide-additive system
Kamochi, Yasuko,Kudo, Tadahiro,Masuda, Toshinobu,Takadate, Akira
, p. 1017 - 1020 (2007/10/03)
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.
