- Pd-Catalyzed C-H Halogenation of Indolines and Tetrahydroquinolines with Removable Directing Group
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Pd-catalyzed directing-group-assisted regioselective halogenations to C7 of indolines and C8 of tetrahydroquinolines were achieved in good to excellent yields. The practicality and utility of the developed method have been illustrated by various functiona
- Ahmad, Ashfaq,Dutta, Himangsu Sekhar,Kumar, Mohit,Khan, Afsar Ali,Raziullah,Koley, Dipankar
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p. 5870 - 5875
(2020/07/30)
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- Preparing method of aromatic nitrile or alkenyl nitrile compound
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The invention discloses a preparing method of an aromatic nitrile or alkenyl nitrile compound. The preparing method comprises the following step that under protection of inert gas, an aryl or heteroaryl sulphonate compound shown in a formula II or an alkenyl sulphonate compound shown in a formula IV and a cyanation reagent are subjected to a cross-coupling reaction as is shown below in a solvent under the condition of the presence of a nickel complex, metal zinc and an additive to obtain the aromatic nitrile or alkenyl nitrile compound, wherein 4-dimethylamiopryidine (DMAP) is adopted as the additive, and zinc cyanide is adopted as the cyanation reagent. By means of the preparing method, cyanation of aryl sulphonate, heteroaryl sulphonate or alkenyl sulphonate can be simply and efficientlyachieved with a cheap catalysis system; moreover, the functional group compatibility and substrate universality are good, and a better application prospect and higher using value are provided for achieving industrial synthesis of the aromatic nitrile or alkenyl nitrile compound.
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Paragraph 0133-0135; 0172-0174
(2019/10/01)
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- PYRAZOLO-TRIAZINE AND/OR PYRAZOLO-PYRIMIDINE DERIVATIVES AS SELECTIVE INHIBITOR OF CYCLIN DEPENDENT KINASE
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The present invention relates to pyrazolo[1,5-a][1,3,5]triazine and pyrazolo[l,5-a]pyrimidine derivatives and/or pharmaceutically acceptable salts thereof, the use of these derivatives as pharmaceutically active agents, especially for the prophylaxis and/or treatment of cell proliferative diseases, inflammatory diseases, immunological diseases, cardiovascular diseases and infectious diseases. Furthermore, the present invention is directed towards pharmaceutical compositions containing at least one of the pyrazolo[1,5-a][1,3,5]triazine and pyrazolo[1,5-a]pyrimidine derivatives and/or pharmaceutically acceptable salts thereof.
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Page/Page column 50; 82
(2019/11/04)
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- Nickel-Catalyzed Cyanation of Phenol Derivatives with Zn(CN)2 Involving C-O Bond Cleavage
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An efficient nickel-catalyzed cyanation of aryl sulfonates, fluorosulfonates, and sulfamates with Zn(CN)2 was developed, which provides a facile access to the nitrile products in generally good to excellent yields. The reaction is accomplished by using NiII complex as the precatalyst and DMAP as the additive. The method also displays wide functional group compatibility; for example, keto, methoxy, N,N-dimethylamino, cyano, ester, and pyridyl groups are well-tolerated during the reaction process.
- Gan, Yi,Wang, Gaonan,Xie, Xin,Liu, Yuanhong
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p. 14036 - 14048
(2018/11/03)
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- Aryl nitrile compound preparation method
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The present invention provides a preparation method of an aryl nitrile compound having a general formula I, wherein the general formula I is defined in the specification. The preparation method comprises: adopting an aryl compound having a general formula II as a substrate, wherein the general formula II is defined in the specification, n is 0-1, X1, X2, X3 and X4 are independently and respectively any one selected from N, S, O and C in chemically acceptable structures, Y is OSO2F, OTf or OTs, and R1, R2, R3 and R4 are independently and respectively any one selected from H, alkyl, aryl and halogen; and carrying out a cyanation reaction on the aryl compound and a cyanogen source under the catalysis effect of a catalyst, a reducing agent and a ligand to obtain the aryl nitrile compound. With the preparation method of the present invention, the aryl nitrile compound preparation cost can be reduced, the required reaction temperature is low, the requirements on the catalyst is low, the conversion rate is high, and the preparation method is suitable for various aryl or miscellaneous aryl substrates containing electron-rich or electron-deficient substituents.
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Paragraph 0076; 0077; 0078
(2017/06/20)
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- Synthesis of nitriles from aldehydes with trimethylphenylammonium tribromide and ammonium acetate
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Various aromatic and heterocyclic aldehydes were easily converted to respective nitriles with the combination of trimethylphenylammonium tribromide and ammonium acetate in good yields at room temperature.
- Sayama, Shinsei
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p. 1796 - 1802
(2016/11/06)
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- Aerobic Copper-Promoted Radical-Type Cleavage of Coordinated Cyanide Anion: Nitrogen Transfer to Aldehydes to Form Nitriles
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We have disclosed for the first time the copper-promoted C≡N triple bond cleavage of coordinated cyanide anion under a dioxygen atmosphere, which enables a nitrogen transfer to various aldehydes. Mechanistic study of this unprecedented transformation suggests that the single electron-transfer process could be involved in the overall course. This protocol provides a new cleavage pattern for the cyanide ion and would eventually lead to a more useful synthetic pathway to nitriles from aldehydes.
- Wu, Qian,Luo, Yi,Lei, Aiwen,You, Jingsong
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supporting information
p. 2885 - 2888
(2016/03/19)
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- Iodine-catalyzed ammoxidation of methyl arenes
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The development of organic transformation using cheap and readily available substrates under mild conditions will be pivotal for green and sustainable synthetic organic chemistry. Concerning our continued interest in the cyanation reaction, a metal-free direct ammoxidation of readily available methyl arenes leading to nitriles was established under mild conditions. A series of aryl methanes especially heteroaryl methanes (30 examples) were applicable in moderate to good yields with good functionality tolerance.
- Guo, Songjin,Wan, Gen,Sun, Song,Jiang, Yan,Yu, Jin-Tao,Cheng, Jiang
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supporting information
p. 5085 - 5088
(2015/03/30)
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- A mild and efficient palladium-catalyzed cyanation of aryl mesylates in water or tBuOH/water
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Cool and compatible: Aryl mesylates and tosylates underwent palladium-catalyzed cyanation under mild, aqueous conditions at 65-80°C (see scheme). In many cases, water could be used as the reaction medium without a cosolvent, and a variety of substituents R, such as keto, aldehyde, ester, free amine, and nitrile groups, remained intact during the transformation. Cy=cyclohexyl, Ms=methanesulfonyl, Ts=p-toluenesulfonyl.
- Yeung, Pui Yee,So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 8918 - 8922
(2011/02/24)
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- Design, synthesis, and evaluation in vitro of quinoline-8-carboxamides, a new class of poly(adenosine-diphosphate-ribose)polymerase-1 (PARP-1) inhibitor
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Poly(ADP-ribose)polymerase-1 is an important target enzyme in drug design; inhibitors have a wide variety of therapeutic activities. A series of quinoline-8-carboxamides was designed to maintain the required pharmacophore conformation through an intramolecular hydrogen bond. 3-Substituted quinoline-8-carboxamides were synthesized by Pd-catalyzed couplings (Suzuki, Sonogashira, Stille) to 3-iodoquinoline-8-carboxamide, an efficient process that introduces diversity in the final step. 2-Substituted quinoline-8-carboxamides were prepared by selective Pd-catalyzed couplings at the 2-position of 2,8-dibromoquinoline, followed by lithium-bromine exchange of the intermediate 2-(alkyl/aryl)-8-bromoquinolines and reaction with trimethylsilyl isocyanate. The intramolecular hydrogen bond was confirmed by X-ray and by NMR. The SAR of the 3-substituted compounds for inhibition of human recombinant PARP-1 activity showed a requirement for a small narrow group. Substituents in the 2-position increased potency, with the most active 2-methylquinoline-8-carboxamide having IC50 = 500 nM (IC50 = 1.8 μM for 5-aminoisoquinolin-1- one (5-AIQ, a standard water-soluble inhibitor)).
- Lord, Anna-Marie,Mahon, Mary F.,Lloyd, Matthew D.,Threadgill, Michael D.
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experimental part
p. 868 - 877
(2009/11/30)
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- An environmentally benign procedure for the synthesis of aryl and arylvinyl nitriles assisted by microwave in ionic liquid
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Aryl and arylvinyl nitriles have been prepared in good yields from the corresponding bromides with potassium hexacyanoferrate (II) using palladium-catalyzed reactions in ionic liquid under microwave irradiation. Georg Thieme Verlag Stuttgart.
- Li, Lian-Hua,Pan, Zhen-Liang,Duan, Xin-Hua,Liang, Yong-Min
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p. 2094 - 2098
(2008/02/05)
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- Cooperative catalyst effects in palladium-mediated cyanation reactions of aryl halides and triflates
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Substoichiometric quantities of copper or zinc species dramatically improve both conversion rate and efficiency of Pd(0)-catalyzed cyanation reactions. The optimum reaction conditions involve the use of a nitrile solvent, NaCN, and a catalyst system employing the combination of cuprous iodide with tetrakis(triphenylphosphine)palladium(0), [Pd(PPh3)4]. Beneficial effects were observed for the conversion of aryl halides, aryl triflates, and a vinyl bromide to the corresponding nitriles. The process was demonstrated on preparative scale with a broad range of aromatic and heteroaromatic substrates containing diverse functionality. A dual catalytic cycle is proposed to explain the profound influences of the cocatalyst system.
- Anderson, Benjamin A.,Bell, Edward C.,Ginah, Francis O.,Harn, Nancy K.,Pagh, Lisa M.,Wepsiec, James P.
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p. 8224 - 8228
(2007/10/03)
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- Nucleophilic Displacement Catalyzed by Transition Metal. IX. *CHCl3-DPPF Catalyzed Cyanation of Aryl Halides and Aryl Triflates
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A catalyst system comprising *CHCl3 and DPPF was proved to be efficient for the cyanation of aryl iodides and aryl triflates with KCN.The reactivities of aryl substrates decreased in the order ArI > ArOTf > ArBr.
- Takagi, Kentaro,Sasaki, Ken,Sakakibara, Yasumasa
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p. 1118 - 1121
(2007/10/02)
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