65185-58-2Relevant articles and documents
Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups
Amberchan, Gabriella,Snelling, Rachel A.,Moya, Enrique,Landi, Madison,Lutz, Kyle,Gatihi, Roxanne,Singaram, Bakthan
supporting information, p. 6207 - 6227 (2021/05/06)
The binary hydride, diisobutylaluminum borohydride [(iBu)2AlBH4], synthesized from diisobutylaluminum hydride (DIBAL) and borane dimethyl sulfide (BMS) has shown great potential in reducing a variety of organic functional groups. This unique binary hydride, (iBu)2AlBH4, is readily synthesized, versatile, and simple to use. Aldehydes, ketones, esters, and epoxides are reduced very fast to the corresponding alcohols in essentially quantitative yields. This binary hydride can reduce tertiary amides rapidly to the corresponding amines at 25 °C in an efficient manner. Furthermore, nitriles are converted into the corresponding amines in essentially quantitative yields. These reactions occur under ambient conditions and are completed in an hour or less. The reduction products are isolated through a simple acid-base extraction and without the use of column chromatography. Further investigation showed that (iBu)2AlBH4 has the potential to be a selective hydride donor as shown through a series of competitive reactions. Similarities and differences between (iBu)2AlBH4, DIBAL, and BMS are discussed.
GPR40 receptor stimulant, and preparation method, pharmaceutical composition and application thereof
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Paragraph 0163-0168, (2019/10/15)
The invention discloses a GPR40 receptor stimulant, and a preparation method, a pharmaceutical composition and application thereof. The invention particularly discloses a GPR40 receptor stimulant shown in general formula (I) and pharmacologically acceptable salt thereof, a preparation process of the compound, a pharmaceutical composition containing the compound of general formula (I), and application of the compound and the pharmaceutical composition in anti-diabetes.
Design, synthesis and biological evaluation of a series of novel GPR40 agonists containing nitrogen heterocyclic rings
Sun, Zhaozhu,Zhou, Tian,Pan, Xuan,Yang, Ying,Huan, Yi,Xiao, Zhiyan,Shen, Zhufang,Liu, Zhanzhu
supporting information, p. 3050 - 3056 (2018/08/11)
A novel series of GPR40 agonists is designed by introducing nitrogen-containing heterocyclic ring at the terminal phenyl ring of TAK-875 with the aim of decreasing its lipophilicity. Three different β-substituted phenylpropionic acids were investigated as the acidic components. A total of 34 compounds have been synthesized, among which, compound 30 exhibited comparable GPR40 agonistic activity in vitro with TAK-875 and relatively lower lipophilicity through calculation (30, EC50 = 1.2 μM, cLogP = 1.3; TAK-875: EC50 = 5.1 μM, cLogP = 3.4). Moreover, compound 30 was able to enhance the insulin secretion of primary islets isolated from normal ICR mice and showed no obvious inhibition against cytochromes P450 in vitro. In vivo, compound 30 exhibited efficacy in oral glucose tolerance test (oGTT) in normal ICR mice.
Fe3O4-SiO2-P4VP pH-sensitive microgel for immobilization of nickel nanoparticles: An efficient heterogeneous catalyst for nitrile reduction in water
Nabid, Mohammad Reza,Bide, Yasamin,Niknezhad, Mahvash
, p. 538 - 546 (2014/03/21)
Fe3O4 magnetic nanoparticles (MNPs) were modified with (3-aminopropyl)triethoxysilane through silanization. An atom transfer radical polymerization-initiating site immobilized onto amine-functionalized Fe3O4 MNPs. The surface-initiated atom transfer radical polymerization of 4-vinylpyridine was then performed in the presence of Fe 3O4-SiO2-Br nanoparticles, which led to the formation of Fe3O4-SiO2-P4VP [P4VP=poly(4-vinylpyridine)] hybrid microgels cross-linked with Fe 3O4 MNPs. Our approach uses polymer microgels as templates for the synthesis of nickel nanoparticles (NiNPs). The tunable properties of synthesized NiNPs@Fe3O4-SiO2-P4VP pH-sensitive microgels were used in the catalytic reduction of aliphatic and aromatic nitriles. Moreover, the catalytic activity of metal nanocomposites that can be modulated by the volume transition of microgel structures with changing pH has been evaluated. TEM, X-ray photoelectron spectroscopy, thermogravimetric analysis, atomic absorption spectroscopy, XRD, UV/Vis spectroscopy, and FTIR spectroscopy were used to characterize the resultant catalyst. Mystery solved: Our approach uses polymer microgels as templates for the synthesis of nickel nanoparticles. The tunable properties of synthesized NiNPs@Fe3O 4-SiO2-P4VP [NiNPs=nickel nanoparticles; P4VP=poly(4-vinylpyridine)] pH-sensitive microgels are used in the catalytic reduction of aliphatic and aromatic nitriles. Moreover, the catalytic activity of metal nanocomposites that can be modulated by the volume transition of microgel structures with changing pH has been evaluated. Copyright
Concise copper-catalyzed synthesis of tricyclic biaryl ether-linked aza-heterocyclic ring systems
Mestichelli, Paola,Scott, Matthew J.,Galloway, Warren R. J. D.,Selwyn, Jamie,Parker, Jeremy S.,Spring, David R.
, p. 5448 - 5451 (2013/11/19)
A new method for the synthesis of tricyclic biaryl ether-linked ring systems incorporating seven-, eight-, and nine-membered ring amines is presented. In the presence of catalytic quantities of copper(I), readily accessible acyclic precursors undergo an intramolecular carbon-oxygen bond-forming reaction facilitated by a templating chelating nitrogen atom. The methodology displays a broad substrate scope, is practical, and generates rare and biologically interesting tricyclic heteroaromatic products that are difficult to access by other means.
Improved protocol for indoline synthesis via palladium-catalyzed intramolecular C(sp2)-H amination
He, Gang,Lu, Chengxi,Zhao, Yingsheng,Nack, William A.,Chen, Gong
supporting information; experimental part, p. 2944 - 2947 (2012/08/28)
An efficient method has been developed for the synthesis of indoline compounds from picolinamide (PA)-protected β-arylethylamine substrates via palladium-catalyzed intramolecular amination of ortho-C(sp2)-H bonds. These reactions feature high efficiency, low catalyst loadings, mild operating conditions, and the use of inexpensive reagents.
HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
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Page/Page column 180; 181, (2011/04/14)
Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.
Reductions of aliphatic and aromatic nitriles to primary amines with diisopropylaminoborane
Haddenham, Dustin,Pasumansky, Lubov,DeSoto, Jamie,Eagon, Scott,Singaram, Bakthan
experimental part, p. 1964 - 1970 (2009/07/01)
Diisopropylaminoborane [BH2Nf)Pr)2] in the presence of a catalytic amount of lithium borohydride (LiBH4) reduces a large variety of aliphatic and aromatic nitriles in excellent yields. BH 2NOPr)2 can be prepared by two methods: first by reacting diisopropylamineborane [(iPr)2N)BH3] with 1.1 equiv of n-butylhthium (n-BuLi) followed by methyl iodide (MeI), or reacting iPrN:BH 3 with 1 equiv of n-BuLi followed by trimethylsilyl chloride (TMSCl). BH2N(ZPr)2 prepared with MeI was found to reduce benzonitriles to the corresponding benzylamines at ambient temperatures, whereas diisopropylaminoborane prepared with TMSCl does not reduce nitriles unless a catalytic amount of a lithium ion source, such as LiBH4 or lithium tetraphenylborate (LiBPh4), is added to the reaction. The reductions of benzonitriles with one or more electron-withdrawing groups on the aromatic ring generally occur much faster with higher yields. For example, 2,4-dichlorobenzonitrile was successfully reduced to 2,4-dichlorobenzylamine in 99% yield after 5 h at 25 °C. On the other hand, benzonitriles containing electron-donating groups on the aromatic ring require refluxing in tetrahydrofuran (THF) for complete reduction. For instance, 4- methoxybenzonitrile was successfully reduced to 4-methoxybenzylamine in 80% yield. Aliphatic nitriles can also be reduced by the BH2N(iPr) 2/cat. LiBH4 reducing system. Benzyl cyanide was reduced to phenethylamine in 83% yield. BH2NOPr)2 can also reduce nitriles in the presence of unconjugated alkenes and alkynes such as the reduction of 2-hexynenitrile to hex-5-yn-l-amine in 80% yield. Unfortunately, selective reduction of a nitrile in the presence of an aldehyde is not possible as aldehydes are reduced along with the nitrile. However, selective reduction of the nitrile group at 25 °C in the presence of an ester is possible as long as the nitrile group is activated by an electron-withdrawing substituent. It should be pointed out that lithium aminoborohydrides (LABs) do not reduce nitriles under ambient conditions and behave as bases with aliphatic nitriles as well as nitriles containing acidic a-protons. Consequently, both LABs and BH2NOPr)2 are complementary to each other and offer methods for the selective reductions of multifunctional compounds.
Lewis acid-catalyzed intramolecular amination via 1,3-chirality transfer
Kawai, Nobuyuki,Abe, Ryuzou,Uenishi, Jun'Ichi
scheme or table, p. 6580 - 6583 (2011/02/23)
Direct intramolecular amination of the chiral non-racemic allylic alcohol 1 conjugated with a benzene ring afforded the tetrahydroisoquinoline 2 possessing a newly formed alkene in the presence of a catalytic amount of Lewis acid.
