- Construction of a benzo[b]azepine skeleton through decarboxylative ylide [6+1] annulations with modified vinyl benzoxazinanones
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A Lewis acid-promoted [6+1] annulation between sulfur ylides and modified vinyl benzoxazinanones was described. In this reaction, the newly designed vinyl benzoxazinanones could serve as a novel six-atom synthon, and the key to success is the installation of an electron-withdrawing group on the alkene moiety of the benzoxazinanones. A broad range of substrates are compatible with this mild reaction system, thereby providing a facile and practical approach for constructing a benzo[b]azepine skeleton.
- Li, Qing-Zhu,Jia, Zhi-Qiang,Chen, Lin,Zhang, Xiang,Leng, Hai-Jun,Zeng, Rong,Liu, Yan-Qing,Zou, Wen-Lin,Li, Jun-Long
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supporting information
p. 814 - 818
(2021/02/16)
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- Access to 5,6-Spirocycles Bearing Three Contiguous Stereocenters via Pd-Catalyzed Stereoselective [4 + 2] Cycloaddition of Azadienes
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We present herein a highly diastereo- and enantioselective Pd-catalyzed [4 + 2] cycloaddition of benzofuran-derived azadienes with vinyl benzoxazinanones, which represents a rare highly stereoselective cycloaddition of this class of fused azadienes as a two-atom synthon. The use of a phosphoramidite ligand bearing a chiral secondary amine with a simple biphenyl backbone proved to be the key to construct the novel spirocyclic tetrahydroquinoline scaffold containing three contiguous stereocenters as a single diastereomer in high enantioselectivity.
- Fairuz Binte Sheikh Ismail, Siti Nur,Yang, Binmiao,Zhao, Yu
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supporting information
p. 2884 - 2889
(2021/05/05)
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- Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement
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α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate α-imino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities through cascade reactions in one pot.
- Li, Ling,Zhang, Shiqi,Deng, Xiongfei,Li, Guangxun,Tang, Zhuo,Zhao, Gang
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supporting information
p. 6819 - 6824
(2021/09/08)
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- A [4+3] Cycloaddition Reaction of Aza-ortho-quinone Methides with C,N-Cyclic Azomethine Imines for Synthesis of 1,2,4-Triazepines
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The base-induced formal [4+3] cycloaddition reaction of C,N-cyclic azomethine imines with aza-ortho-quinone methides, generated in situ, is reported. This protocol provided an efficient method for the synthesis of biologically important 1,2,4-triazepine derivatives, with a wide substrate scope and excellent functional-group tolerance, and it gives moderate to excellent yields under mild conditions. Several of the derivatives exhibited in vitro antitumor activities against the A2780 cell line in a screening of the cancer cell lines HCT-116, H2228, and A2780 by an MTT assay.
- Wang, Xinyue,Li, Zefei,Feng, Chang,Zhen, Qi,Guo, Mingzhang,Yao, Yaning,Zou, Xinyu,Wang, Pengfei,Hou, Yunlei,Gong, Ping
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supporting information
p. 2090 - 2096
(2021/09/06)
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- Red phosphorescent compounds and organic electroluminescence device prepared by using compounds
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The invention discloses red phosphorescent compounds and an organic electroluminescence device prepared by using the compounds. In the organic electroluminescence device including an anode, a hole injection layer, a hole transport layer, a light emitting
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Paragraph 0061-0063
(2020/02/19)
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- Visible-light-induced radical isocyanide insertion protocol for the synthesis of difluoromethylated spiro[indole-3,3′-quinoline] derivatives
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Herein, we report the first protocol for visible-light-induced radical isocyanide insertion reactions between 3-(2-isocyanobenzyl)-indoles and bromodifluoroacetates or bromodifluoroacetamides. The protocol, which has good functional group tolerance and a broad substrate scope, constitutes an efficient and general route to difluoromethylated spiro[indole-3,3′-quinoline] derivatives. This journal is
- Zhang, Jingjing,Xu, Wentao,Qu, Yi,Liu, Yuxiu,Li, Yongqiang,Song, Hongjian,Wang, Qingmin
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supporting information
p. 15212 - 15215
(2020/12/21)
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- Palladium-Catalyzed Regioselective Syn-Chloropalladation-Olefin Insertion-Oxidative Chlorination Cascade: Synthesis of Dichlorinated Tetrahydroquinolines
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A palladium catalyzed cascade process involving syn-chloropalladation, intramolecular olefin insertion, and oxidative C-Cl bond formation reactions was demonstrated for the synthesis of dichlorinated tetrahydroquinolines in high yields (up to 93%). The N-propargyl arylamines having a tethered α,β-unsaturated carbonyl moiety underwent a regioselective syn-chloropalladation followed by a Heck-type reaction to deliver the tetrahydroquinoline scaffold. The rare insertion of the second chlorine atom was rationalized comprising a PdII/IV catalytic cycle and oxidative cleavage of the C-PdII bond.
- Vinoth, Perumal,Karuppasamy, Muthu,Vachan,Muthukrishnan, Isravel,Maheswari, C. Uma,Nagarajan, Subbiah,Pace, Vittorio,Roller, Alexander,Bhuvanesh, Nattamai,Sridharan, Vellaisamy
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supporting information
(2019/05/08)
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- Sequential Phosphine-Catalyzed [4 + 2] Annulation of β′-Acetoxy Allenoates: Enantioselective Synthesis of 3-Ethynyl-Substituted Tetrahydroquinolines
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The first enantioselective sequential phosphine-catalyzed (SPC as abbreviation) mode for the formation of tetrahydroquinolines with an ethynyl-substituted all-carbon quaternary stereogenic center is reported. In this SPC process, a novel [4 + 2] annulation process was devised employing α-substituted allenoates as C2 synthons (α-β′, 1,2-dipole) for the first time. 3-Ethynyl-substituted tetrahydroquinolines were readily prepared in good yields and high enantioselectivities.
- Zhang, Qinglong,Jin, Hongxing,Feng, Jiaxu,Zhu, Yannan,Jia, Penghao,Wu, Chengzhou,Huang, You
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supporting information
p. 1407 - 1411
(2019/03/07)
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- Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes
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Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.
- Wales, Steven M.,Rivinoja, Daniel J.,Gardiner, Michael G.,Bird, Melissa J.,Meyer, Adam G.,Ryan, John H.,Hyland, Christopher J. T.
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supporting information
p. 4703 - 4708
(2019/06/27)
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- Asymmetric [4+2] cycloaddition of azlactones with dipolar copper–allenylidene intermediates for chiral 3,4-dhydroquinolin-2-one derivatives
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In this paper, a pybox-copper catalyzed enantioselective decarboxylative [4+2] cycloaddition reaction of ethynyl benzoxazinanones with azlactones has been developed, which provides optically active 3,4-dihydroquinolin-2-ones in high yields with good enantioselectivities and diastereoselectivities. In this transformation, the chiral dipolar copper–allenylidene intermediates are kinetically generated via decarboxylative ethynyl benzoxazinanones, followed by the attack of the enolate azlactones to form enantiomerically enriched 3,4-dihydroquinolin-2-one structures.
- Sun, Bing-Bing,Hu, Qing-Xian,Hu, Jia-Ming,Yu, Jie-Qiang,Jia, Jun,Wang, Xing-Wang
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supporting information
p. 1967 - 1970
(2019/06/27)
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- Red phosphorescence compound and organic light-emitting diode device prepared by using red phosphorescence compound
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The invention discloses a red phosphorescence compound and an organic electroluminescent device prepared by using the red phosphorescence compound. The structural formula of the red phosphorescence compound provided by the invention is shown as the formul
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Paragraph 0045; 0046; 0047
(2019/01/08)
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- Highly Diastereoselective Synthesis of Trifluoromethyl Indolines by Interceptive Benzylic Decarboxylative Cycloaddition of Nonvinyl, Trifluoromethyl Benzoxazinanones with Sulfur Ylides under Palladium Catalysis
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A highly diastereoselective synthesis of trifluoromethyl-substituted indolines under palladium catalysis is disclosed. The reaction proceeds by interceptive decarboxylative benzylic cycloaddition (IDBC) of nonvinyl, trifluoromethyl benzoxazinanones with sulfur ylides. The palladium-π-benzyl zwitterionic intermediates are suggested for this transformation, and this would be the first example of an IDBC reaction.
- Punna, Nagender,Das, Pulakesh,Gouverneur, Véronique,Shibata, Norio
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supporting information
p. 1526 - 1529
(2018/03/23)
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- PhI(OAc)2-mediated dearomative C-N coupling: Facile construction of the spiro[indoline-3,2′-pyrrolidine] skeleton
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A facile construction of the spiro[indole-3,2′-pyrrolidine] skeleton, through diacetoxyiodobenzene (PIDA) mediated C-N bond-forming dearomatization of C3 sulfonamide linked indole derivatives, has been developed. A variety of spiro-indolepyrrolidines were
- Zhou, Yali,Li, Dengke,Tang, Shi,Sun, Hongwei,Huang, Jinbo,Zhu, Qiang
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supporting information
p. 2039 - 2042
(2018/03/27)
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- Enantioselective Organocatalytic Intramolecular Aza-Diels–Alder Reaction
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A highly efficient catalytic enantioselective intramolecular Povarov reaction was developed with primary anilines as 2-azadiene precursors. A wide variety of angularly fused azacycles were obtained without column chromatography in high to excellent yields and with excellent diastereo- and enantioselectivity (d.r.>99:1 and up to e.r. 99:1). Furthermore, the catalyst loading could be lowered to 1 mol %, and the obtained azacycles could be used as key intermediates for further transformations to generate additional molecular diversity.
- Jarrige, Lucie,Blanchard, Florent,Masson, Géraldine
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supporting information
p. 10573 - 10576
(2017/08/22)
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- Easy Access to Quinolin-2(1 H)-ones via a One-Pot Tandem Oxa-Michael-Aldol Sequence
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An efficient strategy for the synthesis of a variety of quinolin-2(1 H)-one derivatives has been developed. The reaction proceeded from cinnamide derivatives via a tandem reaction in the presence of NaOH to afford the corresponding 2- quinolin-2(1 H)-one derivatives in good to excellent yields.
- Jarrige, Lucie,Merad, Jeremy,Zaied, Siwar,Blanchard, Florent,Masson, Géraldine
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supporting information
p. 1724 - 1728
(2017/10/06)
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- Catalytic Asymmetric Construction of the Tryptanthrin Skeleton via an Enantioselective Decarboxylative [4 + 2] Cyclization
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The first catalytic asymmetric construction of the tryptanthrin skeleton has been established, taking advantage of a palladium(0)/chiral ligand-catalyzed enantioselective decarboxylative [4 + 2] cyclization of vinyl benzoxazinanones with isatins. This rea
- Mei, Guang-Jian,Bian, Chen-Yu,Li, Guo-Hao,Xu, Shao-Li,Zheng, Wen-Qin,Shi, Feng
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supporting information
p. 3219 - 3222
(2017/06/23)
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- Pd(II)-catalyzed enantioselective intramolecular oxidative amination utilizing (+)-camphorsulfonic acid
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An enantioselective Pd(II)-catalyzed intramolecular oxidative amination reaction was developed utilizing the commercially available chiral X-type ligand (1S)-(+)-camphorsulfonic acid. The Wacker-type cyclization produced chiral indoline products with enantioselectivies up to 45% ee. Electronic structure calculations employing density functional theory support a trans-aminopalladation mechanism.
- Aebly, Andrew H.,Rainey, Trevor J.
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supporting information
p. 3795 - 3799
(2017/09/15)
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- Asymmetric synthesis of isoquinolinonaphthyridines catalyzed by a chiral Br?nsted acid
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A catalytic asymmetric method for the synthesis of chiral isoquinolinonaphthyridines has been developed. A chiral disulfonimide catalyzes a redox cyclization reaction between 2-methyl-3-aldehydeazaarenes and 1,2,3,4-tetrahydroisoquinolines to deliver a range of isoquinolinonaphthyridines with good to high yields (up to 91%) and up to 92:8 er.
- Li, Jianjun,Fu, Yiwei,Qin, Cong,Yu, Yang,Li, Hao,Wang, Wei
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supporting information
p. 6474 - 6477
(2017/08/16)
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- Amphoteric 2-(sulfonylamino)benzaldehydes, secondary amines and isocyanides in the multicomponent synthesis of elusive N-alkyl-2,3-diaminoindoles
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A novel interrupted Ugi reaction between ortho-sulfonylaminated aryl aldehydes, secondary amines, and isocyanides affords in good to high yields N-alkyl-2,3-diaminoindoles, providing access to a so far unexplored area of the indole chemical space. With only one single chemical operation, this novel reaction affords a broad gamma of substituted 2,3-diaminoindoles with five points of diversity. The success of this novel multicomponent transformation lies in presence of the amphoteric sulfonylamino group, which sequentially acts as a Br?nsted acids and as a nucleophile the lack of need for additional catalysts and the high atom economy, with the loss of only one molecule of water, renders this approach a very effective one.
- Giustiniano, Mariateresa,Pelliccia, Sveva,Sangaletti, Luca,Meneghetti, Fiorella,Amato, Jussara,Novellino, Ettore,Tron, Gian Cesare
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supporting information
p. 4264 - 4268
(2017/10/11)
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- Sunlight-Driven Forging of Amide/Ester Bonds from Three Independent Components: An Approach to Carbamates
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A photoredox catalytic route to carbamates enabled by visible irradiation (or simply sunlight) has been developed. This process leads to a novel approach to the construction of heterocyclic rings wherein the amide or ester motifs of carbamates were assembled from three isolated components. Large-scale experiments were realized by employing continuous flow techniques, and reuse of photocatalyst demonstrated the green and sustainable aspects of this method.
- Zhao, Yating,Huang, Binbin,Yang, Chao,Chen, Qingqing,Xia, Wujiong
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supporting information
p. 5572 - 5575
(2016/11/17)
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- Cycloadditions with Bromo-Substituted Morita-Baylis-Hillman Adducts of Isatins and N-(ortho-Chloromethyl)aryl Amides
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Efficient construction of a challenging aza-spirocycloheptane oxindole scaffold is reported through an unprecedented [4 + 3] cycloaddition reaction with bromo-substituted Morita-Baylis-Hillman adducts of isatins and N-(ortho-chloromethyl)aryl amides. Both reactive intermediates, the allylic phosphonium ylides and aza-o-quinone methides, were in situ generated, chemoselectively facilitated by a Lewis base and Bronsted base, respectively.
- Zhan, Gu,Shi, Ming-Lin,He, Qing,Du, Wei,Chen, Ying-Chun
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supporting information
p. 4750 - 4753
(2015/10/12)
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- Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl α,β-unsaturated ketones: Construction of chiral functionalized tetrahydroquinolines
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The diastereo- and enantioselective synthesis of 2,3,4-trisubstituted tetrahydroquinolines has been developed through organocatalytic domino aza-Michael-Michael reaction of o-N-tosylaminophenyl α,β-unsaturated ketones with nitroalkenes. This useful and simple domino process afforded diverse highly functionalized tetrahydroquinolines, some of which are not easily accessible using other methodologies, in good yields and with excellent diastereo- and enantioselectivities (up to >30:1 dr, >99% ee).
- Kim, Shinae,Kang, Ki-Tae,Kim, Sung-Gon
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supporting information
p. 5114 - 5121
(2014/07/08)
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- Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl α,β-unsaturated ketones: Construction of chiral functionalized tetrahydroquinolines
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The diastereo- and enantioselective synthesis of 2,3,4-trisubstituted tetrahydroquinolines has been developed through organocatalytic domino aza-Michael-Michael reaction of o-N-tosylaminophenyl α,β-unsaturated ketones with nitroalkenes. This useful and simple domino process afforded diverse highly functionalized tetrahydroquinolines, some of which are not easily accessible using other methodologies, in good yields and with excellent diastereo- and enantioselectivities (up to >30:1 dr, >99% ee).
- Kim, Shinae,Kang, Ki-Tae,Kim, Sung-Gon
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supporting information
p. 5114 - 5121
(2014/12/10)
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- One-pot catalytic enantioselective synthesis of functionalized tetrahydroquinolines by aza-michael/michael cascade reactions of N-protected 2-aminophenyl α,β-unsaturated esters with Nitroolefins
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A highly enantioselective synthesis of functionalized tetrahydroquinolines with useful biological properties has been developed by means of asymmetric organocatalytic aza-Michael/Michael cascade reactions of nitroolefins with N-protected 2-aminophenyl α,β-unsaturated esters in the presence of a chiral thiourea catalyst. The reaction gave the corresponding highly functionalized tetrahydroquinolines in good yields, excellent diastereoselectivities (>30:1 dr), and high enantioselectivities (≤99% ee).
- Kang, Ki-Tae,Kim, Sung-Gon
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supporting information
p. 3365 - 3373
(2015/01/09)
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- N-heterocyclic carbene-catalyzed enantioselective intramolecular N-tethered aldehyde-ketone benzoin reactions
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The N-heterocyclic carbene-catalyzed enantioselective intramolecular benzoin reaction of N-tethered substrates was realized. With 15 mol % of d-camphor-derived triazolium salt E and 10 mol % of NaOAc, the aldehyde-ketone cross benzoin reactions of various substituted N-tethered substrates proceeded smoothly to afford dihydroquinolinone derivatives with a quaternary carbon stereocenter in moderate to good yields and excellent ee.
- Jia, Min-Qiang,You, Shu-Li
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supporting information
p. 622 - 624
(2013/05/09)
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- Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands
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We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.
- Ida, Yoshihiro,Matsubara, Ayaka,Nemoto, Toru,Saito, Manabu,Hirayama, Shigeto,Fujii, Hideaki,Nagase, Hiroshi
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p. 5810 - 5831
(2012/11/06)
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- Preparation of triazolobenzodiazepine derivatives as Vasopressin V1a antagonists
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This Letter describes the synthesis of a number of fused tricyclic and bicyclic triazolobenzodiazepines for the Vasopressin V1a antagonist programme.
- Beal, David M.,Bryans, Justin S.,Johnson, Patrick S.,Newman, Julie,Pasquinet, Christelle,Peakman, Torren M.,Ryckmans, Thomas,Underwood, Toby J.,Wheeler, Simon
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body text
p. 5913 - 5917
(2011/11/14)
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- GLYCINE B ANTAGONISTS
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The invention relates to quinoline derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are glycine B antagonists and are therefore useful for the control and prevention of various disorders, including neurological disorders.
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Page/Page column 44
(2010/04/27)
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- Substituent effects upon the catalytic activity of aromatic cyclic seleninate esters and spirodioxyselenuranes that act as glutathione peroxidase mimetics
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(Chemical Equation Presented) Substituent effects were studied in a series of aromatic cyclic seleninate esters and spirodioxyselenuranes that function as mimetics of the antioxidant selenoenzyme glutathione peroxidase. The methoxy-substituted selenurane proved the most efficacious catalyst for the reduction of hydrogen peroxide with benzyl thiol, and the reaction rates were enhanced for both classes by electron-donating substituents. Hammett plots indicated ρ = -0.45 and -3.1 for the seleninates and selenuranes, respectively, suggesting that oxidation at Se is the rate-determining step in their catalytic cycles.
- Press, David J.,Mercier, Eric A.,Kuzma, Dusan,Back, Thomas G.
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p. 4252 - 4255
(2008/09/20)
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- The Synthesis of 1,2,7,11b-Tetrahydroisoxazolobenzodiazepin-6(5H)-ones and 1,3,3a,9b-Tetrahydroisoxazoloquinolin-4(5H)-ones
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The reaction of various ethyl 3-carbamoyl>acrylates (2) with electron deficient olefins proceeds via a sequential dipole formation, dipolar cycloaddition sequence to furnish the tetrahydroisoxazolobenzodiazepin-6(5H)-ones and tetrahydroisoxazoloquinolin-4(5H)-ones (4) and (6).The product distribution reflects the nature of the reacting olefin and the position and extent of substitution on the acrylate moiety.
- Bourke, Sharon,Heaney, Frances
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p. 7527 - 7530
(2007/10/02)
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- Benzoxazine herbicides
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2-amino-4H-3,1 benzoxazines, e.g. 6-chloro 2-dimethylamino-4H, 3,1-benzoxazine, are useful as herbicides. The compounds may be prepared by reacting an amine with a 2-halomethylphenyl isocyanate.
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