- Three-Component Couplings among Heteroarenes, Difluorocyclopropenes, and Water via C-H Activation
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Three-component couplings have been realized for efficiently constructing various nitrogen-containing skeletons via C-H activation, where difluorocyclopropenes have been first identified as coupling partners. Many substrates including sp2 and sp3 C-H substrates were well tolerated, furnishing the corresponding products in good yields. Furthermore, a catalyst-dependent reaction was also developed, enabling divergent construction of two different frameworks. The application value of these reactions was demonstrated in gram-scale experiments with as little as 1 mol % catalyst.
- Liu, Xuexin,Chen, Jian,Yang, Chunyan,Wu, Zhouping,Li, Zhiyang,Shi, Yuesen,Huang, Tianle,Yang, Zhongzhen,Wu, Yong
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supporting information
p. 6831 - 6835
(2021/09/08)
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- RhIII-Catalyzed Direct Heteroarylation of C(sp3)-H and C(sp2)-H Bonds in Heterocycles with N-Heteroaromatic Boronates
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Herein, we disclose a RhIII-catalyzed heteroarylation of C(sp3)-H and C(sp2)-H bonds in heterocycles with organoboron reagents. This protocol displays high efficiency and excellent functional group tolerance. A range of heterocyclic boronates with strong coordinating atoms, including pyridine, pyrimidine, pyrazole, thiophene, and furan derivatives, can be extensively served as the coupling reagents. The direct heteroarylation method could supply potential application in terms of the synthesis of drug molecules with multiple heterocycles.
- Wang, Huai-Wei,Wu, Jia-Xue,Qiao, Yu-Han,Li, Yong-Fei,Li, Da-Cheng,Dou, Jian-Min,Yao, Qing-Xia,Lu, Yi
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supporting information
p. 7177 - 7182
(2021/09/18)
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- 1H-PYRAZOLO[4,3-d]PYRIMIDINE COMPOUNDS AS TOLL-LIKE RECEPTOR 7 (TLR7) AGONISTS
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Compounds according to formula I are useful as agonists of Toll-like receptor 7 (TLR7). Such compounds can be used in cancer treatment, especially in combination with an anti-cancer immunotherapy agent, or as a vaccine adjuvant.
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Paragraph 00140-00141
(2021/08/06)
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- Rh(iii)-Catalyzed straightforward arylation of 8-methyl/formylquinolines using diazo compounds
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A straightforward Rh(iii)-catalyzed general strategy was developed for the introduction of naphthol/phenol moieties to the C(sp3)-H bond of 8-methylquinoline using diazonaphthalen-2(1H)-ones/quinone diazides. The developed method was further extended towards the arylation of 8-formylquinolines to accomplish diarylketone derivatives. The method is simple, relatively rapid, and chemo and regioselective with a wide scope and functional group tolerance. The synthetic utility was established through gram-scale synthesis and biologically active molecule construction.
- Ghosh, Bidhan,Samanta, Rajarshi
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supporting information
p. 6886 - 6889
(2019/06/18)
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- Palladium-Catalyzed C-H Bond Functionalization Reactions Using Phosphate/Sulfonate Hypervalent Iodine Reagents
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A new and operationally simple approach for palladium-catalyzed C-H functionalization reactions utilizing an organophosphorus/sulfonate hypervalent iodine reagent as both an oxidant and the source of a functional group has been developed. Through this method, the oxidative phosphorylation-, sulfonation-, and hydroxylation of unactivated benzyl C(sp3)-H bonds, along with the hydroxylation and arylation of aryl C(sp2)-H bonds, are successfully realized under mild conditions and with excellent site-selectivity. The versatile C-OSO2R bond provides a platform for a wide array of subsequent diversification reactions.
- He, Yimiao,Huang, Lilan,Xie, Limei,Liu, Peng,Wei, Qiongmei,Mao, Fangfang,Zhang, Xuehong,Huang, Jun,Chen, Sijing,Huang, Chusheng
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p. 10088 - 10101
(2019/08/22)
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- Corrigendum: Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles (Chemistry - A European Journal, (2017), 23, 57, (14167-14172), 10.1002/chem.201703642)
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The authors have been alerted to an error that was unfortunately missed at the time of publication. Table was duplicated with Table 4. The correct version of Table 2 is shown below. The authors apologise for any inconvenience caused. Organo-photoredox catalyzed oxidative dehydrogenation of tetrahydroquinolines (THQ).[a,b] (Table presented.) [a] Reaction conditions: 1 (0.5 mmol), rose bengal (1.0 mol %), N,N-dimethylacetamide (2.0 mL), open air atmosphere under visible-light irradiation at room temperature for 24 h. [b] Isolated yields. [c] 0.1 mol % of photoredox catalyst for 28 h.
- Sahoo, Manoj K.,Jaiswal, Garima,Rana, Jagannath,Balaraman, Ekambaram
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p. 7038 - 7038
(2019/05/17)
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- TLR7/8 ANTAGONISTS AND USES THEREOF
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The present invention relates to compounds of Formula I and pharmaceutically acceptable compositions thereof, useful as TLR7/8 antagonists.
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-
Paragraph 0216; 0311; 0312
(2019/02/05)
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- Cp?Rh(III)-Catalyzed Mild Addition of C(sp3)-H Bonds to α,β-Unsaturated Aldehydes and Ketones
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A Rh(III)-catalyzed addition of benzylic C(sp3)-H bond to α,β-unsaturated ketones/aldehydes has been realized, leading to efficient synthesis of γ-aryl ketones/aldehydes. This atom-economic reaction proceeded under mild and redox-neutral conditions with a broad substrate scope. Besides benzylic C-H, allylic C-H bonds are also applicable when assisted by O-methyl ketoxime directing groups.
- Liu, Bingxian,Hu, Panjie,Zhou, Xukai,Bai, Dachang,Chang, Junbiao,Li, Xingwei
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supporting information
p. 2086 - 2089
(2017/04/28)
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- Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles
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We report here for the first time the catalytic oxidative dehydrogenation of N-heterocycles by a visible-light organo-photoredox catalyst with low catalyst loading (0.1–1 mol %). The reaction proceeds efficiently under base- and additive-free conditions with ambient air at room temperature. The utility of this benign approach is demonstrated by the synthesis of various pharmaceutically relevant N-heteroarenes such as quinoline, quinoxaline, quinazoline, acridine, and indole.
- Sahoo, Manoj K.,Jaiswal, Garima,Rana, Jagannath,Balaraman, Ekambaram
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supporting information
p. 14167 - 14172
(2017/10/16)
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- Cobalt(III)-Catalyzed Alkylation of Primary C(sp3)–H Bonds with Diazo Compounds
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Chelation-assisted C(sp2)–H metalation/carbenoid insertion has been well investigated. However, the analogous carbene functionalization of C(sp3)–H bonds remains a great challenge. Here we report the first cobalt(III)-catalyzed alkyl
- Yan, Sheng-Yi,Ling, Peng-Xiang,Shi, Bing-Feng
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supporting information
p. 2912 - 2917
(2017/09/08)
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- Rh-Catalyzed Direct Amination of Unactivated C(sp3)?H bond with Anthranils Under Mild Conditions
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C?N Bond formation is of great significance due to the ubiquity of nitrogen-containing compounds. Here, a mild and efficient RhIII-catalyzed C(sp3)?H aryl amination reaction is reported. Anthranil is employed as the nitrogen source with 100 % atom efficiency. This C?H amination reaction exhibits broad substrate scope without using any external oxidants. Mechanistic studies including rhodacycle intermediates, H–D exchange, kinetic isotope effect (KIE) experiments, and in situ IR are presented.
- Tang, Conghui,Zou, Miancheng,Liu, Jianzhong,Wen, Xiaojin,Sun, Xiang,Zhang, Yiqun,Jiao, Ning
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supporting information
p. 11165 - 11169
(2016/08/03)
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- Rhodium(III)-catalyzed intermolecular amidation with azides via C(sp 3)-H functionalization
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The amidation reactions of 8-methylquinolines with azides catalyzed by a cationic rhodium(III) complex proceed efficiently to give quinolin-8- ylmethanamine derivatives in good yields via C(sp3)-H bond activation under external oxidant-free conditions. A catalytically competent five-membered rhodacycle has been isolated and characterized, revealing a key intermediate in the catalytic cycle.
- Wang, Nuancheng,Li, Renhe,Li, Liubo,Xu, Shansheng,Song, Haibin,Wang, Baiquan
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p. 5379 - 5385
(2014/06/23)
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- Iridium-catalyzed intermolecular amidation of sp3 C-H bonds: Late-stage functionalization of an unactivated methyl group
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Reported herein is the iridium-catalyzed direct amidation of unactivated sp3 C-H bonds. With sulfonyl and acyl azides as the amino source, the amidation occurs efficiently under mild conditions over a wide range of unactivated methyl groups with high functional group tolerance. This procedure can be successfully applied for the direct introduction of an amino group into complex compounds and thus can serve as a powerful synthetic tool for late-stage C-H functionalization.
- Kang, Taek,Kim, Youngchan,Lee, Donggun,Wang, Zhen,Chang, Sukbok
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p. 4141 - 4144
(2014/04/03)
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- NOVEL HETEROCYCLIC CARBOXAMIDES AS MODULATORS OF KINASE ACTIVITY
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The invention provides novel heterocyclic carboxamide compounds compounds according to Formula (I) their manufacture and use for the treatment of hyperproliferative diseases, such as cancer.
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Page/Page column 31-32
(2013/07/05)
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- INSECTICIDAL COMPOUNDS BASED ON ISOAZOLINE DERIVATIVES
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The present invention relates to compounds of formula (I): Wherein A1, A2, A3, A4, G1, L, Y1, Y2, Y3, Y4, R1, R2, R3 and R
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Page/Page column 38
(2012/09/25)
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- INSECTICIDAL COMPOUNDS BASED ON ISOXAZOLINE DERIVATIVES
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The present invention relates to compounds of formula (I): Wherein A1, A2, A3, A4, G1, L, Y1, Y2, Y3, Y4, R1, R2, R3 and R
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Page/Page column 81
(2011/06/25)
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- Allosteric inhibitors of hepatitis C virus NS5B polymerase thumb domain site II: Structure-based design and synthesis of new templates
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Chronic hepatitis C virus (HCV) infections are a significant medical problem worldwide. The NS5B Polymerase of HCV plays a central role in virus replication and is a prime target for the discovery of new treatment options. We recently disclosed 1H-benzo[d
- Malancona, Savina,Donghi, Monica,Ferrara, Marco,Martin Hernando, Josè I.,Pompei, Marco,Pesci, Silvia,Ontoria, Jesus M.,Koch, Uwe,Rowley, Michael,Summa, Vincenzo
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experimental part
p. 2836 - 2848
(2010/07/04)
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- DERIVATIVES OF QUINOLINES AND QUINOXALINES AS PROTEIN TYROSINE KINASE INHIBITORS
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The invention relates to compounds of Formula (I), wherein the substituens are as defined in the specification, in free form or in the form of a pharmaceutically acceptable salt, solvate, ester, N-oxide thereof; processes for the preparation thereof; to p
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Page/Page column 162; 163
(2009/12/27)
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- QUINAZOLINE DERIVATIVES AS ANTIVIRAL AGENTS
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The present invention relates to the use of quinazoline derivatives of formula (I) wherein A, B, R1, R2, R3 and R4 are defined herein, and pharmaceutically acceptable salts thereof, for the treatment or preventi
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Page/Page column 34
(2010/11/26)
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- 8-Methylquinoline palladacycles: Stable and efficient catalysts for carbon-carbon bond formation
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Cyclopalladated, phosphine free, 8-methyl quinoline based complexes (2a-j) are excellent catalysts for the Heck vinylation of aryl iodides and bromides with turnover numbers of greater than 25 million observed in some cases. The catalysts are air and moisture stable.
- Evans, Paul,Hogg, Paul,Grigg, Ronald,Nurnabi, Mohamed,Hinsley, Joanne,Sridharan, Visuvanathar,Suganthan, Selvaratnam,Korn, Stewart,Collard, Simon,Muir, Jane E.
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p. 9696 - 9704
(2007/10/03)
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- BROMINATION OF QUINOLINE DERIVATIVES WITH N-BROMOSUCCINIMIDE. ISOMERIC COMPOSITION OF THE BROMINATION PRODUCTS BY PMR AND GLC
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The bromination of quinoline and substituted quinolines with N-bromosuccinimide in concentrated H2SO4 takes place exclusively in the homocyclic part.Bromo-substituted quinolines can be obtained by this method.The bromination products were identified by PMR spectroscopy.The differences among the mono-, di-, and trisubstituted (in the benzene ring) compounds were established on the basis of the type of spectrum of the protons of the homocyclic part of the molecule.The compositions of the reaction mixtures were studied by GLC.
- Tochilkin, A. I.,Kovel'man, I. R.,Prokof'ev, E. P.,Gracheva, I. N.,Levinskii, M. V.
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p. 892 - 897
(2007/10/02)
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- SYNTHESIS AND BROMINATION OF 8-METHYLQUINOLINE-5-CARBOXYLIC ACID
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8-Methylquinoline-5-carboxylic acid was obtained by the Skraup reaction from 3-amino-p-toluic acid or by hydrolysis of 5-cyano-8-methylquinoline.The latter was synthesized by the Rosemund-von Braun reaction from 5-bromo-8-methylquinoline, which was obtained by bromination of 8-methylquinoline in the presence of silver sulfate.Bromination in the side chain of 8-methylquinoline-5-carboxylic acid and its nitrile was studied.
- Gracheva, I.N.,Tochilkin, A.I.
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p. 275 - 277
(2007/10/02)
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