- Nickel-Catalyzed Aminoxylation of Inert Aliphatic C(sp3)-H Bonds with Stable Nitroxyl Radicals under Air: One-Pot Route to α-Formyl Acid Derivatives
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Nickel-catalyzed aminoxylation of an unactivated C(sp3)-H bond with a stable nitroxyl radical has been accomplished for the first time to offer various N-alkoxyamine derivatives, which further enables a one-pot approach to α-formyl acid derivatives. The aminoxylation process reported also provides direct evidence for the oxidative addition of a cyclometallic intermediate with a free radical, which is helpful for the reaction-mechanism study in transition-metal-catalyzed functionalization of inert C(sp3)-H bonds.
- Wang, Chunxia,Zhang, Luoqiang,You, Jingsong
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Read Online
- Mechanism of 8-Aminoquinoline-Directed Ni-Catalyzed C(sp3)-H Functionalization: Paramagnetic Ni(II) Species and the Deleterious Effect of Carbonate as a Base
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Studies into the mechanism of 8-aminoquinoline-directed nickel-catalyzed C(sp3)-H arylation with iodoarenes were carried out, to determine the catalyst resting state and optimize catalytic performance. Paramagnetic complexes undergo the key C-H activation step. The ubiquitous base Na2CO3is found to hinder catalysis; replacement of Na2CO3with NaOtBu gave improved catalytic turnovers under milder conditions. Deprotonation of the 8-aminoquinoline derivativeN-(quinolin-8-yl)pivalamide (1a) at the amide nitrogen using NaH, followed by reaction with NiCl2(PPh3)2allowed for the isolation of complex Ni([AQpiv]-κN,N)2(3) with chelating N-donors (where [AQpiv] = C9NH6NCOtBu). Complex3is a four-coordinate disphenoidal high-spin Ni(II) complex, excluding short anagostic Ni-tBu hydrogen interactions. Complex3reacts with the paddle-wheel [Ph3PNi(μ-CO2tBu)2]2(6·PPh3) ortBuCO2H to give insoluble {[AQpiv]Ni(O2CtBu)}2(5). Dissolution of5in donor solvents L (L= DMSO and DMF) gave a paramagnetic intermediate assigned by NMR as [AQpiv]Ni(O2CtBu)L (5·L) and equilibrium reformation of3and6·L. DFT calculations support this equilibrium in solution. Both3and5undergo C-H activation at temperatures as low as 80 °C and in the presence of PR3(PR3= PPh3, PiBu3) to give Ni(C9NH6NCOCMe2CH2-κN,N,C)PR3(7·PR3). The C-H functionalization reaction orders with respect to7·PiBu3, iodoarenes, and phosphines were determined. Hammett analysis using electronically different aryl iodides suggests a concerted oxidative addition mechanism for the C-H functionalization step; DFT calculations were also carried out to support this finding. When Na2CO3is used as the base, the rate determination step for C-H functionalization appears to be 8-aminoquinoline deprotonation and binding to Ni. The carbonate anion was also observed to provide a deleterious NMR-inactive low-energy off-cycle resting state in catalysis. Replacement of Na2CO3with NaOtBu improved catalysis at milder conditions and made carboxylic acid and phosphine additives unnecessary. Complex3and its functionalized analogues were observed as the catalyst resting state under these conditions.
- Liu, Junyang,Johnson, Samuel A.
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p. 2970 - 2982
(2021/06/28)
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- Copper-Catalyzed Oxidative Benzylic C(sp3)?H Cyclization for the Synthesis of β-Lactams
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β-Lactams are important structural motifs because of their ubiquity in natural products and pharmaceuticals. We report herein a Cu-catalyzed intramolecular oxidative C(sp3)?H amidation for the synthesis of β-lactams using tBuOOtBu. This method
- Nozawa-Kumada, Kanako,Saga, Satoshi,Matsuzawa, Yuta,Hayashi, Masahito,Shigeno, Masanori,Kondo, Yoshinori
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supporting information
p. 4496 - 4499
(2020/04/10)
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- Pd/Cu-Catalyzed Cascade C(sp3)-H Arylation and Intramolecular C-N Coupling: A One-Pot Synthesis of 3,4-2 H-Quinolinone Skeletons
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In this letter, we successfully explored a cascade Pd/Cu-catalyzed intermolecular C(sp3)-H arylation of amides and intramolecular C-N coupling reaction. This method provides a one-pot strategy to synthesize 3,4-2H-quinolinone with good regioselectivity of C-H arylation and C-N coupling from C-I and C-X bonds from readily available starting materials.
- Xiao, Han-Zhi,Wang, Wen-Shu,Sun, Yu-Song,Luo, Hao,Li, Bo-Wen,Wang, Xiao-Dong,Lin, Wei-Li,Luo, Fei-Xian
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supporting information
p. 1668 - 1671
(2019/03/11)
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- Palladium-catalyzed 2-pyridylmethyl-directed β-C(sp3)–H activation and cyclization of aliphatic amides with gem-dibromoolefins: A rapid access to γ-lactams
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The direct Pd-catalyzed β-C(sp3)–H activation and cyclization of aliphatic amides bearing a removable 2-pyridylmethyl directing group with gem-dibromoolefins is described for the first time to construct a variety of γ-lactams. The resulting products with Z- and E-configurations can be easily separated and purified after the reaction, demonstrating the effectiveness and applicability of the method herein developed.
- Zhou, Danni,Wang, Chunxia,Li, Mingliang,Long, Zheng,Lan, Jingbo
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p. 191 - 193
(2017/11/17)
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- Nickel-catalysed direct alkylation of thiophenes via double C(sp3)-H/C(sp2)-H bond cleavage: The importance of KH2PO4
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A Ni-catalyzed oxidative C-H/C-H cross-dehydrogenative coupling (CDC) reaction was developed for constructing various highly functionalized alkyl (aryl)-substituted thiophenes. This method employs thiophenes and aliphatic (aromatic) amides that contain an 8-aminoquinoline as a removable directing group in the presence of a silver oxidant. The approach enables the facile one-step synthesis of substituted thiophenes with high functional group compatibility via double C-H bond cleavage without affecting C-Br and C-I bonds. DFT calculations verify the importance of KH2PO4 as an additive for promoting C-H bond cleavage and support the involvement of a Ni(iii) species in the reaction.
- Wang, Xie,Xie, Peipei,Qiu, Renhua,Zhu, Longzhi,Liu, Ting,Li, You,Iwasaki, Takanori,Au, Chak-Tong,Xu, Xinhua,Xia, Yuanzhi,Yin, Shuang-Feng,Kambe, Nobuaki
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p. 8316 - 8319
(2017/07/26)
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- Copper(II)-mediated intermolecular amination of inert C(sp3)[sbnd]H bonds with simple alkylamines to construct α,α-disubstituted β-amino acid derivatives
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Disclosed herein is a copper(II)-mediated chelation-assisted intermolecular amination of inert C(sp3)[sbnd]H bonds using simple alkylamines as the amino source. A straightforward and step-economic alternative to α,α-disubstituted β-amino acid derivatives is provided consequently. This reaction features good functional group tolerance and relatively broad substrate scope. Furthermore, a coupling product between morpholine and radical inhibitor 2,6-di-tert-butyl-p-cresol (BHT) was isolated, indicating that a single electron transfer (SET) process might be involved in this transformation.
- Wang, Chunxia,Yang, Yudong
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supporting information
p. 935 - 940
(2017/02/18)
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- Difluoromethylation of carboxylic acids via the addition of difluorinated phosphorus ylide to acyl chlorides
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A one-step protocol for the difluoromethylation of carboxylic acids is described. The reaction involves the interaction of intermediate acyl chlorides with in situ generated difluorinated phosphorus ylide Ph3P=CF2. Aromatic acids can be selectively transformed within one step either to bis-difluoromethylated alcohols or to difluorinated ketones depending on the particular reaction conditions. For bulky α-branched carboxylic acids, only ketones are produced.
- Trifonov, Alexey L.,Levin, Vitalij V.,Struchkova, Marina I.,Dilman, Alexander D.
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supporting information
p. 5304 - 5307
(2017/11/06)
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- Thioamide-Directed Cobalt(III)-Catalyzed Selective Amidation of C(sp3)?H Bonds
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A mild, oxidant-free, and selective Cp*CoIII-catalyzed amidation of thioamides with robust dioxazolone amidating agents via C(sp3)?H bond activation to generate the desired amidated products is reported. The method is efficient and allows for the C?H amidation of a wide range of functionalized thioamides with aryl-, heteroaryl-, and alkyl-substituted dioxazolones under the Cp*CoIII-catalyzed conditions. The observed regioselectivity towards primary C(sp3)?H activation is supported by computational studies and the cyclometalation is proposed to proceed by means of an external carboxylate-assisted concerted metalation/deprotonation mechanism. The reported method is a rare example of the use of a directing group other than the commonly used pyridine and quinolone classes for Cp*CoIII-catalyzed C(sp3)?H functionalization and the first to exploit thioamides.
- Tan, Peng Wen,Mak, Adrian M.,Sullivan, Michael B.,Dixon, Darren J.,Seayad, Jayasree
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supporting information
p. 16550 - 16554
(2017/12/07)
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- A C-H Insertion Approach to Functionalized Cyclopentenones
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Cyclopentenones are synthetically versatile structures, and their straightforward construction from alkynone substrates by employing synthetically streamlining C-H insertion is conceptually appealing and of high synthetic potential. But, its implementation is very limited. Herein we report a Au-catalyzed version, which affords 2-bromocyclopent-2-en-1-ones with a broad scope and synthetically desirable diastereoselectivities. The proposed key intermediate capable of the observed insertion into unactivated C-H bonds is a fully functionalized gold vinylidene, which is generated via a novel intermolecular strategy. This flexible access of likely gold vinylidenes opens various opportunities to explore their versatile reactivities.
- Wang, Youliang,Zarca, Maxence,Gong, Liu-Zhu,Zhang, Liming
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p. 7516 - 7519
(2016/07/06)
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- Copper(II)/Silver(I)-Catalyzed Sequential Alkynylation and Annulation of Aliphatic Amides with Alkynyl Carboxylic Acids: Efficient Synthesis of Pyrrolidones
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A highly efficient protocol for the synthesis of pyrrolidones by the copper-catalyzed alkynylation/annulation of aliphatic amides with alkynyl carboxylic acids is discussed in this paper. A broad range of easily accessible alkynyl carboxylic acids were introduced at the β-methyl group of aliphatic amides with the assistance of an 8-aminoquinolyl auxiliary group via decarboxylation to achieve the subsequent cyclic C-N bond formation within one hour. High selectivity of β-methyl groups over methylene groups was observed, and the extension of this catalytic system to the activation of methylene C-H bonds failed. The substrates with two different groups at the α-position of the aliphatic amides lead to the formation of diastereoisomers which is determined by 1H NMR spectroscopy. The initially produced products with Z-configurations can be easily transformed to the corresponding products with E-configurations by the treatment with dilute p-toluenesulfonic acid after the reaction. This catalytic tandem decarboxylative cyclization provides a new opportunity for the direct functionalization of sp3 C-H bonds.
- Zhang, Jitan,Li, Danyang,Chen, Hui,Wang, Binjie,Liu, Zhanxiang,Zhang, Yuhong
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supporting information
p. 792 - 807
(2016/03/09)
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- Nickel-Catalyzed Addition-Type Alkenylation of Unactivated, Aliphatic C-H Bonds with Alkynes: A Concise Route to Polysubstituted γ-Butyrolactones
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(Chemical Equation Presented). Through the nickel-catalyzed chelation-assisted C-H bond activation strategy, the addition-type alkenylation of unreactive β-C(sp3)-H bonds of aliphatic amides with internal alkynes is developed for the first time to produce γ,δ-unsaturated carboxylic amide derivatives. The resulting alkenylated products can further be transformed into polysubstituted γ-butyrolactones with pyridinium chlorochromate (PCC).
- Li, Mingliang,Yang, Yudong,Zhou, Danni,Wan, Danyang,You, Jingsong
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p. 2546 - 2549
(2015/05/27)
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- Method for producing hematopoietic stem cells using pyrazole compounds
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An expanding agent for hematopoietic stem cells and/or hematopoietic progenitor cells useful as a therapy for various hematopoietic diseases and useful for improvement in the efficiency of gene transfer into hematopoietic stem cells for gene therapy is provided. A method of producing hematopoietic stem cells and/or hematopoietic progenitor cells, which comprises expanding hematopoietic stem cells by culturing hematopoietic stem cells ex vivo in the presence of a compound represented by the formula following (I), a tautomer or pharmaceutically acceptable salt of the compound or a solvate thereof (wherein R1 to R8 are as defined in the description).
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- Nickel-catalyzed direct thioetherification of β-C(sp3)-H bonds of aliphatic amides
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The nickel-catalyzed β-thioetherification of unactivated C(sp3)-H bond of propionamides is established with the assistance of 8-aminoquinoline auxiliary, leading to the β-thio carboxylic acid derivatives. A broad range of functional groups is compatible with this thioetherfication reaction. The process represents the first successful example of metal-catalyzed C-S bond formation from unactivated C(sp3)-H bonds.
- Lin, Cong,Yu, Wenlong,Yao, Jinzhong,Wang, Bingjie,Liu, Zhanxiang,Zhang, Yuhong
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supporting information
p. 1340 - 1343
(2015/03/14)
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- Nickel-catalyzed direct thiolation of C(sp3)-H bonds in aliphatic amides
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Nickel-catalyzed thiolation of the inactivated methyl C(sp3)-H bonds of aliphatic amides with disulfide is described. It is a novel strategy for the synthesis of thioethers with the ultimate goal of generating thioether carboxylic acids with various functional groups.
- Wang, Xie,Qiu, Renhua,Yan, Chunyang,Reddy, Vutukuri Prakash,Zhu, Longzhi,Xu, Xinhua,Yin, Shuang-Feng
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supporting information
p. 1970 - 1973
(2015/04/27)
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- Palladium(0)/PAr3-catalyzed intermolecular amination of C(sp3)-H bonds: Synthesis of β-amino acids
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An intermolecular C(sp3)-H amination using a Pd0/PAr3 catalyst was developed. The reaction begins with oxidative addition of R2N-OBz to a Pd0/PAr3 catalyst and subsequent cleavage of a C(sp3)-H bond by the generated Pd-NR2 intermediate. The catalytic cycle proceeds without the need for external oxidants in a similar manner to the extensively studied palladium(0)-catalyzed C-H arylation reactions. The electron-deficient triarylphosphine ligand is crucial for this C(sp3)-H amination reaction to occur.
- He, Jian,Shigenari, Toshihiko,Yu, Jin-Quan
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supporting information
p. 6545 - 6549
(2015/06/08)
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- Copper-mediated aryloxylation and vinyloxylation of β-C(sp3)-H bond of propionamides with organosilanes
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A novel copper-mediated method for the aryloxylation and vinyloxylation of β-C(sp3)-H bonds of propioamides with organosilanes is described. The reaction proceeds with the assistance of an 8-aminoquinolyl auxiliary in a tandem way by the first oxidation of β-C(sp3)-H bonds and subsequent arylation/vinylation to give the aryloxylation/vinyloxylation products. This unusual aryloxy/vinyloxy forming reaction offers a new avenue for the functionalization of unactivated sp3 C-H bonds in organic synthesis.
- Zhang, Jitan,Chen, Hui,Wang, Binjie,Liu, Zhanxiang,Zhang, Yuhong
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supporting information
p. 2768 - 2771
(2015/06/16)
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- Cobalt-Catalyzed Cyclization of Aliphatic Amides and Terminal Alkynes with Silver-Cocatalyst
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A new method of cobalt-catalyzed synthesis of pyrrolidinones from aliphatic amides and terminal alkynes was discovered through a C-H bond functionalization process on unactivated sp3 carbons with the silver cocatalyst using a bidentate auxiliary. For the first time, a broad range of easily accessible alkynes are exploited as the reaction partner in C(sp3)-H bond activation to give the important 5-ethylidene-pyrrolidin-2-ones in a site-selective fashion. The reaction tolerates a wide variety of functional groups including -F, -Cl, -Br, -CF3, ether, cyclopropane, and thiophene. Both pyridine ligand and aromatic solvent play the important role for the promotion of reactivity. This cobalt-catalyzed cyclization reaction can be successfully extended to a variety of aromatic amides to afford a variety of isoindolinones. Attractive features of this catalytic system include its low cost, easy operation, and convenient access to a wide range of pyrrolidinones and isoindolinones.
- Zhang, Jitan,Chen, Hui,Lin, Cong,Liu, Zhanxiang,Wang, Chen,Zhang, Yuhong
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supporting information
p. 12990 - 12996
(2015/10/28)
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- Nickel-Catalyzed Direct C (sp3)-H Arylation of Aliphatic Amides with Thiophenes
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Nickel-catalyzed heteroarylation of the inactive methyl C(sp3)-H bond of aliphatic amide with heteroarenes is described. The method takes advantage of chelation assistance by an 8-aminoquinolinyl moiety. The synthetic reaction has good tolerance toward functional groups, and it can be used in the construction of various kinds of alkyl-substituted heteroarenes.
- Wang, Xie,Zhu, Longzhi,Chen, Sihai,Xu, Xinhua,Au, Chak-Tong,Qiu, Renhua
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supporting information
p. 5228 - 5231
(2015/11/18)
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- Iron-catalyzed C(sp2)-H and C(sp3)-H arylation by triazole assistance
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Modular 1,2,3-triazoles enabled iron-catalyzed C-H arylations with broad scope. The novel triazole-based bidentate auxiliary is easily accessible in a highly modular fashion and allowed for user-friendly iron-catalyzed C(sp 2)-H functionalizations of arenes and alkenes with excellent chemo- and diastereoselectivities. The versatile iron catalyst also proved applicable for challenging C(sp3)-H functionalizations, and proceeds by an organometallic mode of action. The triazole-assisted C-H activation strategy occurred under remarkably mild reaction conditions, and the auxiliary was easily removed in a traceless fashion. Intriguingly, the triazole group proved superior to previously used auxiliaries. With a little help: A versatile iron catalyst allows the arylation of C(sp2)-H and C(sp3)-H bonds in the presence of a modular and removable triazolyldimethylmethyl (TAM) auxiliary, whose structure can be varied through 1,3-dipolar azide-alkyne cycloadditions.
- Gu, Qing,Al Mamari, Hamad H.,Graczyk, Karolina,Diers, Emelyne,Ackermann, Lutz
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supporting information
p. 3868 - 3871
(2014/05/06)
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- β-Arylation of carboxamides via iron-catalyzed C(sp3)-H bond activation
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A 2,2-disubstituted propionamide bearing an 8-aminoquinolinyl group as the amide moiety can be arylated at the β-methyl position with an organozinc reagent in the presence of an organic oxidant, a catalytic amount of an iron salt, and a biphosphine ligand at 50 C. Various features of selectivity and reactivity suggest the formation of an organometallic intermediate via rate-determining C-H bond cleavage rather than a free-radical-type reaction pathway.
- Shang, Rui,Ilies, Laurean,Matsumoto, Arimasa,Nakamura, Eiichi
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p. 6030 - 6032,3
(2013/05/22)
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- PYRAZOLE COMPOUNDS HAVING THERAPEUTIC EFFECT ON MULTIPLE MYELOMA
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Novel therapeutic agents for myeloma are provided. A therapeutic agent for multiple myeloma containing a pyrazole compound represented by the formula (1): wherein R1 is C1-C6 alkyl, C1-C6 alkyl substituted with R17, C1-C6 haloalkyl, phenyl, phenyl substituted with a R11's or the like, R2 is a hydrogen atom, C1-C6 alkyl, phenyl or phenyl optionally substituted with e R21's or the like, R3 is a hydrogen atom or the like, X is a single bond or —(CR6, R7)n—, each of R4 and R5 is independently C1-C6 alkyl or the like, R6 and R7 are hydrogen atoms or C1-C6 alkyl, R8 is phenyl, phenyl optionally substituted with k R81's or the like, a tautomer of the compound or a pharmaceutically acceptable salt or solvate thereof, as an active ingredient.
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- Highly regioselective carbonylation of unactivated C(sp3)-H bonds by ruthenium carbonyl
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The regioselective carbonylation of unactivated C(sp3)-H bonds of aliphatic amides was achieved using Ru3(CO)12 as a catalyst. The presence of a 2-pyridinylmethylamine moiety in the amide is crucial for a successful reaction. The reaction shows a preference for C-H bonds of methyl groups as opposed to methylene C-H bonds and tolerates a variety of functional groups. The stoichiometric reaction of an amide with Ru 3(CO)12 gave a dinuclear ruthenium complex in which the 2-pyridinylmethylamino moiety was coordinated to the ruthenium center in an N,N manner.
- Hasegawa, Nao,Charra, Valentine,Inoue, Satoshi,Fukumoto, Yoshiya,Chatani, Naoto
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p. 8070 - 8073
(2011/07/08)
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- Pd(II)-catalyzed carbonylation of C(sp3)-H bonds: A new entry to 1,4-dicarbonyl compounds
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Pd(II)-catalyzed β-C(sp3)-H carbonylation of N-arylamides under CO (1 atm) has been achieved. Following amide-directed C(sp3)-H cleavage and insertion of CO into the resulting [Pd(II)-C(sp3)] bond, intramolecular C-N reductive elimination gave the corresponding succinimides, which could be readily converted to 1,4-dicarbonyl compounds. This method was found to be effective with substrates containing α-hydrogen atoms and could be applied to effect methylene C(sp3)-H carbonylation of cyclopropanes.
- Yoo, Eun Jeong,Wasa, Masayuki,Yu, Jin-Quan
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supporting information; experimental part
p. 17378 - 17380
(2011/02/24)
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- Remote C-H bond functionalization reveals the distance-dependent isotope effect
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Iodination of remote aryl C-H bonds has been achieved using palladium acetate as the catalyst and iodoacetate (IOAc) as the oxidant. Systematic kinetic isotope studies imply a mechanistic regime shift as the number of bonds separating the directing heteroatom and the target C-H bond increases. Both isotope and electronic effects observed in remote C-H bond activation are consistent with an electrophilic palladation pathway in which the initial palladation is slower than the C-H bond cleavage.
- Li, Jiao-Jie,Giri, Ramesh,Yu, Jin-Quan
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p. 6979 - 6987
(2008/09/21)
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- Synthesis of β-, γ-, and δ-lactams via Pd(II)-catalyzed C-H activation reactions
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Pd(II)-catalyzed intramolecular amination of sp2 and sp3 C-H bonds are developed using a combination of CuCl2 and AgOAc as the oxidant. The reaction protocol tolerates the presence of a double bond in the substrates. This catalytic reaction provides practical access to a wide range of β-, γ-, and δ-lactams. Copyright
- Wasa, Masayuki,Yu, Jin-Quan
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supporting information; experimental part
p. 14058 - 14059
(2009/03/11)
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- Pyrazolopyrimidines as therapeutic agents
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The present invention is directed to pyrazolopyrimidine derivatives of formula (I) wherein the substituents are defined herein, which are useful as kinase inhibitors and as such are useful for affecting angiogenesis and diseases and conditions associated with angiogenesis.
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- Radical Chain Reaction or Benzenethiol with Pentynylthiol Esters: Production of Aldehydes under Stannane/Silane-Free Conditions
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The radical chain reaction of benzenethiol with accessible 4-pentynylthiol esters provides a new stannane/silane-free protocol for the production of aromatic and aliphatic aldehydes. The procedure is especially useful for the aryl and primary aldehydes, even in the presence of substituents highly sensitive to reductive conditions, and is also of some utility for the vinylic and secondary ones, The protocol is instead not applicable to the tertiary aldehydes, owing to preferential alkane-forming decarbonylation, although the tertiary ones derived from bridgehead precursors can still be usefully produced.
- Benati, Luisa,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Scialpi, Rosanna,Spagnolo, Piero,Zanardi, Giuseppe
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p. 985 - 990
(2007/10/03)
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- Pyrazolopyrimidines as therapeutic agents
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The present invention provides compounds of Formula I, including pharmaceutically acceptable salts and/or prodrugs thereof, where G, R2, and R3 are defined as described herein.
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- Rates and Mechanism for the Solvolyses of 2,2-Dimethyl-2-sila-1-indanyl Bromide and α-Trialkylsilylbenzyl p-Toluenesulfonates. α-Silicon Effect on the Stability of Benzylic Cations in Solution
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α-Silicon effect on the benzylic solvolysis has been investigated.The solvolysis of 2,2-dimethyl-2-sila-1-indanyl bromide in aq acetone exhibits a linear response to the solvent ionizing power YBr, with a slope m close to unity (m = 0.93) and g
- Shimizu, Nobujiro,Osajima, Erika,Tsuno, Yuho
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p. 1145 - 1152
(2007/10/02)
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- 13,14-Didehydro-PGA1 compounds
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This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
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- 2,2-Difluoro-13,14-didehydro-11-deoxy-17-phenyl-18,19,20-trinor-PGE2 compounds
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This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
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- Cis-13-PGF2α analogs
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This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is of the cis configuration. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
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- 13,14-Didehydro-PG3 compounds
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This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
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- 13,14-Didehydro-PG analogs
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This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
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- 9-Deoxy-PGF2 Analogs
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Prostaglandin analogs with the following cyclopentane ring structure: STR1 are disclosed along with intermediates useful in their preparation and processes for their preparation. These analogs are useful for some of the same pharmacological purposes as the prostaglandins.
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- 4,4,5,5-Tetradehydro-PGE1 analogs
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This invention comprises certain analogs of the prostaglandins in which there is a triple bond between C-5 and C-6 or C-4 and C-5. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
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- Aliphatic 2-decarboxy-2-hydroxymethyl-13,14-didehydro-PG compounds
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This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol and the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
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- 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-PGE, compounds
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This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
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- Phenyl-substituted prostaglandin-F type analogs
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This invention is a group of phenyl-substituted PGE-type, PGF-type, PGA-type and PGB-type compounds, and processes for making them. These compounds are useful for a variety of pharmacological purposes, including anti-ulcer, inhibition of platelet aggregation, increase of nasal patency, labor inducement at term, and wound healing.
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