cas 6590-65-4, N-(2-FORMYLPHENYL)-4-METHYL-BENZENESULF&

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Phosphine-catalyzed [4+1] annulation of 2-tosylaminochalcones with allenoates: Synthesis of trans-2,3-disubstitued indolines
Phosphine-catalyzed [4+1] annulation of 2-tosylaminochalcones with allenoates has been achieved, giving trans-2,3-disubstitued indolines as major diastereoisomers in moderate to good yields.
Gao, Zhenzhen,Wang, Chang,Yuan, Chunhao,Zhou, Leijie,Xiao, Yumei,Guo, Hongchao
p. 12653 - 12656
(2015)
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Ruthenium-catalyzed C-H amination of aroylsilanes
Acylsilane represents a valuable synthon in synthetic chemistry. We report on ruthenium(ii)-catalyzedortho-C-H amination of aroylsilanes to provide facile access to synthetically useful imidobenzoylsilanes and tosyl-amidobenzoylsilanes. The protocols, with broad substrate scope and excellent functional group tolerance, are enabled with the weak chelation-assistance of acylsilaneviaC-H cyclometallation.
He, Rui,Jin, Shuqi,Liao, Yilei,Lu, Xiunan,Shen, Wenzhou,Sun, Yaling,Yu, Feifei,Zhang, Jian,Zhong, Guofu,Zhong, Liangjun
p. 6313 - 6321
(2021)
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A new route to 1,2,3-triazole fused benzooxazepine and benzodiazepine analogues through metal-free intramolecular azide-olefin oxidative cycloaddition
A collection of 1,2,3-triazole fused benzooxazepine and benzodiazepine analogues was prepared by one pot azide substitution and intramolecular azide-olefin oxidative cycloaddition sequence under metal-free conditions.
Gangaprasad,Paul Raj,Karthikeyan,Rengasamy,Kesavan,Vajjiravel,Elangovan
(2019)
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One-Pot Relay Gold(I) and Br?nsted Acid Catalysis: Cyclopenta[b]annulation of Indoles via Hydroamination/Nazarov-Type Cyclization Cascade of Enynols
An expedient relay gold(I) and Br?nsted acid catalyzed hydroamination/Nazarov cyclization of 1-(2-aminophenyl)pent-4-en-2-ynols for the synthesis of various polyfunctionalized cyclopenta[b]indoles is described. The synthetic utility of this method has bee
Dhiman, Seema,Ramasastry
p. 5116 - 5119
(2015)
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Transition metal-free approach to azafluoranthene scaffolds by aldol condensation/[1+2+3] annulation tandem reaction of isocyanoacetates with 8-(alkynyl)-1-naphthaldehydes
A transition metal-free aldol condensation/[1+2+3] annulation reaction of isocyanoacetates with 8-(alkynyl)-1-naphthaldehydes has been developed for the general synthesis of azafluoranthenes. This domino reaction enables successive formation of three new bonds and two rings from readily accessible starting materials in a single operation. Furthermore, this methodology can also be utilized to construct chromeno[4,3-c]pyridines and benzo[c][2,6]naphthyridines in moderate yields.
Dong, Penghui,Majeed, Kashif,Wang, Lingna,Guo, Zijian,Zhou, Fengtao,Zhang, Qiuyu
p. 4855 - 4858
(2021/05/25)

Iron-Catalyzed Electrophilic Amination of Sodium Sulfinates with Anthranils
A practical method for the synthesis of N-(2-carbonylaryl) benzenesulfonamides via an iron-catalyzed electrophilic amination of sodium sulfinates with anthranils is described. This redox-neutral transformation has high atom efficiency and is achieved under simple and mild reaction conditions. A wide range of anthranils and sodium sulfinates were compatible in this transformation. Moreover, the synthetic potential of this methodology was further demonstrated by the synthesis of various useful N-heterocycles and derivatives.
Liang, Baihui,Huang, Junjie,Zhu, Weidong,Li, Yawen,Jiang, Lanping,Gao, Yang,Xie, Feng,Li, Yibiao,Chen, Xiuwen,Zhu, Zhongzhi
p. 1466 - 1473
(2021/02/09)

SUBSTITUTED CHROMANES, ANALOGS THEREOF, AND METHODS OF USE AND SYNTHESIS
Disclosed are chromane compounds, analogs thereof, and methods of their synthesis and use. The compounds may be synthesized by methods involving reductive annulations of arylidene malonates with unsaturated electrophiles using photoredox/Lewis acid cooperative catalysis. The compounds may be formulated in a pharmaceutical composition for treating one of the aforementioned diseases or disorders.
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(2021/01/25)

Design and application of intramolecular vinylogous Michael reaction for the construction of 2-alkenyl indoles
A base-mediated transformation based on a designed intramolecular vinylogous Michael addition (intra-VMA) is presented to access 3-substituted 2-alkenyl indole derivatives. The reaction represents the first example of the intra-VMA for the construction of
Harish, Battu,Yadav, Sanjay,Suresh, Surisetti
supporting information
p. 231 - 234
(2021/01/14)

Copper-Catalyzed (4+1) Cascade Annulation of Terminal Alkynes with 2-(Tosylmethyl)anilines: Synthesis of 2,3-Disubstituted Indoles
A novel strategy based on Cu-catalyzed (4+1) cascade annulation of terminal alkynes as one-carbon synthons with 2-(tosylmethyl)anilines has been developed for the expeditious synthesis of 2,3-disubstituted indoles, in which in situ generations of aza-o-quinone methides and alkynyl-copper(I) species are involved. This annulation provides an effective method for the assembly of synthetically and structurally interesting 2,3-disubstituted indoles.
Yan, Xu,Liu, Chun-Fang,An, Xian-Tao,Ge, Xiao-Min,Zhang, Qing,Pang, Lin-Han,Bao, Xu,Fan, Chun-An
p. 8905 - 8909
(2021/11/24)

Cascade Skeletal Rearrangement of Gold Carbene Intermediates: Synthesis of Medium-Sized Pyrimidine-Fused Benzolactones
A gold-catalyzed cyclization/cascade skeletal rearrangement of o-cyanophenylalkynones with 3-amino-benzo[d]-isoxazoles has been developed, which provides an approach for synthesizing medium-sized benzolactones. Based on the experimental results, we postul
Hu, Xiaoping,Liu, Yuanhong,Wang, Ali,Xie, Xin
supporting information
p. 3769 - 3774
(2021/07/17)

FUSED-GLUTARIMIDE CRBN LIGANDS AND USES THEREOF
The present invention provides compounds, compositions thereof, and methods of using the same. The present invention also relates to compounds and methods useful for binding and modulating the activity of cereblon (CRBN), especially for the inhibition of CRBN, and the treatment of CRBN-mediated disorders.
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(2021/02/12)

Diastereoselective Construction of Cyclopropane-Fused Tetrahydroquinolines via a Sequential [4 + 2]/[2 + 1] Annulation Reaction
A sequential [4 + 2]/[2 + 1] annulation of α-aryl vinylsulfoniums with 2-aminochalcones and 2-(2-aminobenzylidene)-1H-indene-1,3(2H)-dione is reported that affords a series of cyclopropane-fused tetrahydroquinolines. The salient features of this novel and practical transformation include high efficiency, transition-metal-free nature, operational simplicity, and outstanding functional group tolerance.
Wang, Zhen-Hua,Shen, Li-Wen,Xie, Ke-Xin,You, Yong,Zhao, Jian-Qiang,Yuan, Wei-Cheng
supporting information
p. 3114 - 3118
(2020/04/20)

Enantioselective Synthesis of Complex Fused Heterocycles through Chiral Phosphoric Acid Catalyzed Intramolecular Inverse-Electron-Demand Aza-Diels–Alder Reactions
A stable asymmetric intramolecular Povarov reaction has been established to provide an efficient method to access structurally diverse trans,trans-trisubstituted tetrahydrochromeno[4,3-b]quinolines in high stereoselectivities of up to >99:1 diastereomeric
Jarrige, Lucie,Gandon, Vincent,Masson, Géraldine
p. 1406 - 1413
(2020/01/24)

Palladium-Catalyzed Regioselective Syn-Chloropalladation-Olefin Insertion-Oxidative Chlorination Cascade: Synthesis of Dichlorinated Tetrahydroquinolines
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
(2019/05/08)

Direct Access to 9-Chloro-1 H-benzo[ b]furo[3,4- e]azepin-1-ones via Palladium(II)-Catalyzed Intramolecular syn-Oxypalladation/Olefin Insertion/sp2-C-H Bond Activation Cascade
An efficient Pd(II)-catalyzed cascade approach was established for the synthesis of 9-chloro-1H-benzo[b]furo[3,4-e]azepin-1-ones starting from N-propargyl arylamines having a pendant α,β-unsaturated ester scaffold. The mechanism of this sequential process involved intramolecular syn-oxypalladation followed by olefin insertion and ortho sp2-C-Cl bond formation reactions. This high atom- and step-economical cascade sequence generated two heterocycle rings and three new bonds in a single synthetic operation.
Karuppasamy, Muthu,Vachan,Vinoth, Perumal,Muthukrishnan, Isravel,Nagarajan, Subbiah,Ielo, Laura,Pace, Vittorio,Banik, Subrata,Maheswari, C. Uma,Sridharan, Vellaisamy
p. 5784 - 5788
(2019/08/26)

Visible-Light-Driven Neutral Nitrogen Radical Mediated Intermolecular Styrene Difunctionalization
A neutral nitrogen radical-mediation strategy, wherein the existing N-H moiety of substrates serves as a neutral nitrogen radical precursor to enable room-temperature intermolecular radical difunctionalization of styrenes under photoredox catalysis, is reported. The reaction shows high functional group tolerance and substrate scope with respect to both components, giving the corresponding products with generally good yields. Preliminary control experiments and DFT calculations are performed to explain the reaction mechanism.
Zhao, Quan-Qing,Li, Man,Xue, Xiao-Song,Chen, Jia-Rong,Xiao, Wen-Jing
supporting information
p. 3861 - 3865
(2019/05/24)

Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes
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.
p. 4703 - 4708
(2019/06/27)

Asymmetric [4+2] cycloaddition of azlactones with dipolar copper–allenylidene intermediates for chiral 3,4-dhydroquinolin-2-one derivatives
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
p. 1967 - 1970
(2019/06/27)

A nickel(ii)-catalyzed asymmetric intramolecular Alder-ene reaction of 1,7-dienes
A highly diastereo- and enantioselective intramolecular Alder-ene reaction with an alkene as the enophile has been developed by using a chiral N,N′-dioxide/nickel(ii) complex as the catalyst. This protocol provides a facile route towards the synthesis of diverse 3,4-disubstituted chroman, tetrahydroquinoline, piperidine and thiochroman derivatives in high yields with good to excellent diastereo- and enantioselectivities.
Liu, Wen,Zhou, Pengfei,Lang, Jiawen,Dong, Shunxi,Liu, Xiaohua,Feng, Xiaoming
p. 4479 - 4482
(2019/04/26)

Straightforward and Sustainable Synthesis of Sulfonamides in Water under Mild Conditions
Ideally, a sustainable chemical synthesis should involve the use of non-toxic solvents and reactants, easy separations and purification by energy-efficient processes. In this context, reconsidering the synthesis of widely used drugs is especially timely and should allow important benefits to be obtained in terms of environmental impact. Sulfonamides are pertinent as their synthesis generally requires the use of toxic and/or hard-to-remove solvents such as dichloromethane, DMF and DMSO. In addition, toxic and highly reactive sulfur-containing sources such as sulfonyl chloride are often involved and coupled with amines. Moreover, the latter may exhibit some toxicity and are generally difficult to purify. Herein, we disclose the unprecedented and sustainable synthesis of sulfonamides by using sodium sulfinate as a commercial and stable sulfur source and nitroarenes as the nitrogen-containing reactant. In addition, under the optimized conditions only water is used as a “green” solvent and the products are collected by simple filtration.
Eid, Nadim,Karamé, Iyad,Andrioletti, Bruno
supporting information
p. 5016 - 5022
(2018/09/14)

Intramolecular Umpolung Allylation of Imines
An intramolecular umpolung allylation of imines is reported. This reaction occurs via the intermediacy of 2-azaallyl anions. It could proceed either under transition-metal-catalyzed conditions or under transition-metal-free conditions. Importantly, this a
Zhan, Miao,Pu, Xiang,He, Bin,Niu, Dawen,Zhang, Xia
supporting information

(2018/09/27)

Phosphine-Catalyzed Reaction between 2-Aminobenzaldehydes and Dialkyl Acetylenedicarboxylates: Synthesis of 1,2-Dihydroquinoline Derivatives and Toward the Development of an Olefination Reaction
A series of 1,2-dihydroquinolines were synthesized in good to excellent yields by reacting 2-aminobenzaldehyde derivatives and dialkyl acetylenedicarboxylates with catalytic amounts of phosphine. This reaction was rendered catalytic by the selective in situ phosphine oxide reduction with the use of phenylsilane. Furthermore, with the same starting materials and with an additional role of the reducing agent, a new olefination reaction was discovered. Hydrogen/deuterium (H/D) exchange experiments revealed the possible mechanism of this reaction.
Han, Xu,Saleh, Nidal,Retailleau, Pascal,Voituriez, Arnaud
p. 4584 - 4588
(2018/08/09)

Iridium- and Rhodium-Catalyzed Directed C-H Heteroarylation of Benzaldehydes with Benziodoxolone Hypervalent Iodine Reagents
The C-H heteroarylation of benzaldehydes with indoles and pyrroles was realized using the benziodoxolone hypervalent iodine reagents indole- and pyrroleBX. Functionalization of the aldehyde C-H bond using either an o-hydroxy or amino directing group and catalyzed by an iridium or a rhodium complex allowed the synthesis of salicyloylindoles and (2-sulfonamino)benzoylindoles, respectively, with good to excellent yields (74-98%). This new transformation could be carried out under mild conditions (rt to 40 °C) and tolerated a broad range of functionalities, such as ethers, halogens, carbonyls, or nitro groups.
Grenet, Erwann,Waser, Jér?me
p. 1473 - 1476
(2018/03/09)

Divergence in Ynone Reactivity: Atypical Cyclization by 3,4-Difunctionalization versus Rare Bis(cyclization)
Functionalized ynones can be activated by Tf2C=CH2, which was generated in situ, to form zwitterionic species. These species were trapped in an intramolecular fashion by several nucleophiles to generate two major types of triflones in a divergent manner. Through fine-tuning of the reaction temperature, bis(triflyl)-6-membered- or (triflyl)-5-membered-fused-heterocycles were achieved in reasonable yields in a totally selective manner. In this way, bis(triflyl)flavones, bis(triflyl)thioflavones, bis(triflyl)selenoflavones, (triflyl)benzothienopyrans, (triflyl)benzoselenophenopyrans, (triflyl)vinyl aurones, and (triflyl)pyranoindoles were constructed. Conceivable mechanistic pathways were suggested on the basis of the isolation of several intermediates and the results from control experiments.
Alcaide, Benito,Almendros, Pedro,Lázaro-Milla, Carlos,Delgado-Martínez, Patricia
p. 8186 - 8194
(2018/06/15)

Silver-Catalyzed Radical Cascade Cyclization toward 1,5-/1,3-Dicarbonyl Heterocycles: An Atom-/Step-Economical Strategy Leading to Chromenopyridines and Isoxazole-/Pyrazole-Containing Chroman-4-Ones
A novel and convenient silver-catalyzed radical cascade cyclization toward a large variety of 1,5-/1,3-dicarbonyl heterocycles containing a chroman-4-one, indanone, or 2,3-dihydroquinolin-4(1H)-one moiety was developed, by reacting various 2-functionalized benzaldehydes, including 2-allyloxy benzaldehydes, 2-allyl benzaldehyde, and 2-N(Ts)CH2-CH CH2 substituted benzaldehyde, with 1,3-dicarbonyl compounds in the presence of AgNO3/K2S2O8 in one pot under mild reaction conditions. The newly obtained 1,5-/1,3-dicarbonyl-containing heterocycles were further used directly to synthesize more structurally diverse polyheterocycles, mainly including chromenopyridines as well as isoxazole- or pyrazole-containing chroman-4-ones.
Hu, Hao,Chen, Xiaolan,Sun, Kai,Wang, Junchao,Liu, Yan,Liu, Hui,Fan, Lulu,Yu, Bing,Sun, Yuanqiang,Qu, Lingbo,Zhao, Yufen
p. 6157 - 6160
(2018/10/05)

Structure-activity relationship of the cinnamamide family of antibiotic potentiators for methicillin-resistant: Staphylococcus aureus (MRSA)
Methicillin-resistant Staphylococcus aureus (MRSA) is a global public health threat. MRSA has evolved a complex set of biochemical processes that mobilize the organism for inducible resistance on challenge by β-lactam antibiotics. Interfering pharmacologi
Speri, Enrico,Fishovitz, Jennifer,Mobashery, Shahriar
p. 2008 - 2016
(2019/01/04)

Intramolecular Cycloaddition Approach to Fused Pyrazoles: Access to 4,5-Dihydro-2 H -pyrazolo[4,3- c ]quinolines, 2,8-Dihydroindeno[2,1- c ]pyrazoles, and 4,5-Dihydro-2 H -benzo[ e ]indazoles
A straightforward and efficient method for the synthesis of pyrazoles fused with 1,2,3,4-tetrahydroquinoline, 2,3-dihydro-1 H -indene, or 1,2,3,4-tetrahydronaphthalene involves the formation of the tosylhydrazone from an aromatic substrate carrying aldehy
Jash, Moumita,Das, Bimolendu,Sen, Suparna,Chowdhury, Chinmay
supporting information
p. 1511 - 1520
(2017/12/26)

Amphoteric 2-(sulfonylamino)benzaldehydes, secondary amines and isocyanides in the multicomponent synthesis of elusive N-alkyl-2,3-diaminoindoles
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
supporting information
p. 4264 - 4268
(2017/10/11)

Palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes with O2: a facile protocol to selectively synthesize 2- and 3-vinylindoles
A novel palladium-catalyzed oxidative cyclization of aniline-tethered alkylidenecyclopropanes using molecular oxygen as the terminal oxidant through β-carbon elimination of aminopalladation intermediates is disclosed. The reaction opens up an effective way to obtain a series of 2- and 3-vinylindoles which are important synthetic intermediates in many natural indole derivatives.
Cao, Bo,Simaan, Marwan,Marek, Ilan,Wei, Yin,Shi, Min
p. 216 - 219
(2016/12/27)

Synthesis of a novel methyl(2E)-2-{[N-(2-formylphenyl)(4-methylbenzene) sulfonamido]methyl}-3-(2-methoxyphenyl)prop-2-enoate: Molecular structure, spectral, antimicrobial, molecular docking and DFT computational approaches
The title compound methyl(2E)-2-{[N-(2-formylphenyl)(4-methylbenzene)sulfonamido] methyl}-3-(2-methoxyphenyl)prop-2-enoate (MFMSM) has been synthesized and single crystals were grown by slow evaporation solution growth technique at room temperature. XRD,
Murugavel,Vetri velan,Kannan, Damodharan,Bakthadoss, Manickam
p. 457 - 475
(2016/08/12)

Diastereoselective synthesis of 2,4-substituted tetrahydroquinolines via hf(otf)4-catalyzed substitution/cyclization of 2-aminobenzyl alcohols with styrenes
An efficient and convenient stereoselective synthetic approach to 2,4-substituted 1,2,3,4-tetrahydroquinoline has been developed. This catalytic procedure involves a sequential reaction of 2-aminobenzyl alcohol with styrenes in the presence of Hf(OTf)4 ca
Noji, Masahiro,Kadowaki, Hiroto,Kubota, Yuuki,Yoshida, Tomomi,Saito, Noriko,Yamaguchi, Subaru,Ohata, Ren,Ishii, Keitaro,Takanami, Toshikatsu
p. 1041 - 1073
(2017/07/27)

Ir-Catalyzed C?H Amidation of Aldehydes with Stoichiometric/Catalytic Directing Group
Ir-catalyzed sp2C?H amidation of aldehydes with various anilines as stoichiometric or catalytic directing groups was accomplished. A wide range of substrates were selectively amidated in good to excellent yields with broad functional group tolerance. The iridacycle complexes were isolated, characterized, and proved as key intermediates. Kinetic studies and Hammett plots provided detailed understandings of this amidation. According to the mechanism, the electron-rich ArSO2N3was proved effective for intermolecular sp3C?H amidation.
Zhang, Yun-Fei,Wu, Bin,Shi, Zhang-Jie
supporting information
p. 17808 - 17812
(2016/11/28)

Iridium-Catalyzed Direct ortho-C-H Amidation of Benzaldehydes through N-Sulfonyl Imines as Mask
Ir-catalyzed direct C-H sulfamidation of benzaldehydes has been achieved. A series of ortho-amided benzaldehydes were obtained in up to 95% yields for 21 examples with excellent regioselectivity and broad functional group tolerance. This transformation could proceed smoothly with low catalyst loading under external-oxidant-, acid-, or base-free conditions. Molecular nitrogen was released as the sole byproduct, providing an environmentally benign sulfamidation process.
Li, Yudong,Feng, Yadong,Xu, Linhua,Wang, Lianhui,Cui, Xiuling
supporting information
p. 4924 - 4927
(2016/10/18)

Experimental and computational approaches of a novel methyl (2E)-2-{[N-(2-formylphenyl)(4-methylbenzene)sulfonamido]methyl}-3-(4-chlorophenyl)prop-2-enoate: A potential antimicrobial agent and an inhibition of penicillin-binding protein
The title compound methyl(2E)-2-{[N-(2-formylphenyl) (4-methylbenzene)sulfonamido]methyl}-3-(4-chlorophenyl) prop-2-enoate (MFMSC) has been synthesized and single crystals were grown by slow evaporation solution growth technique at room temperature. Struc
Murugavel,Vetri Velan,Kannan, Damodharan,Bakthadoss, Manickam
p. 33 - 54
(2016/03/09)

BENZENE SULFONAMIDE-BASED INHIBITORS OF SPHINGOSINE KINASE
A novel class of sphingosine kinase (SK) inhibitor compounds are disclosed which are useful in the treatment of cancer and other proliferative cell conditions. The compounds are benzene sulfonamides with a chemical structure according to formula (I).
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(2016/03/13)

Convergent synthesis of 2-aryl-substituted quinolines by gold-catalyzed cascade reaction
Gold-catalyzed auto-tandem catalysis has been developed for synthesizing 2-aryl-substituted quinolines. The reaction of an aniline bearing an acetal moiety with an aryl alkyne proceeded via formal [4+2]-cycloaddition, which involved the addition of gold acetylide to an oxonium ion to give amino alkyne intermediate and sequential 6-endo-dig cyclization of amino alkyne intermediate by attacking of nitrogen to alkyne moiety activated by gold catalyst. The cationic gold catalyst promoted two different processes by enhancing the nucleophilicity and electrophilicity of alkyne. This convergent synthetic methodology enabled the synthesis of a variety of 2-aryl-substituted quinolines.
Ueda, Hirofumi,Yamaguchi, Minami,Tokuyama, Hidetoshi
p. 824 - 829
(2016/07/14)

The Synthesis of 5-Amino-dihydrobenzo[b]oxepines and 5-Amino-dihydrobenzo[b]azepines via Ichikawa Rearrangement and Ring-Closing Metathesis
The combination of Ichikawa's rearrangement and a ring-closing metathesis reaction of allyl carbamates is presented as a method for the preparation of 5-amino-substituted 2,5-dihydro-benzo[b]oxepines, 2,5-dihydro-benzo[b]azepines, and 2,5-dihydro-benzo[b]thiepins. It was demonstrated that the use of nonracemic allyl carbamates enables the synthesis of enantioenriched benzo-fused seven-membered heterocycles. Finally, it was shown that further functionalization of the obtained structures allows access to pharmacologically active 5-amino-substituted 2,3,4,5-tetrahydro-1-benzo[b]oxepine scaffolds.
Chwastek, Monika,Pieczykolan, Micha?,Stecko, Sebastian
p. 9046 - 9074
(2016/10/17)

Synthesis, crystal structure analysis, spectral investigations, DFT computations, Biological activities and molecular docking of methyl(2E)-2-{[N-(2-formylphenyl)(4-methylbenzene) sulfonamido]methyl}-3-(4-fluorophenyl)prop-2-enoate, a potential bioactive
The title compound methyl(2E)-2-{[N-(2-formylphenyl) (4-methylbenzene)sulfonamido]methyl}-3-(4-fluorophenyl) prop-2-enoate (MFMSF) has been synthesized and single crystals were grown by slow evaporation solution growth technique at room temperature. The g
Murugavel,Vetri Velan,Kannan, Damodharan,Bakthadoss, Manickam
p. 150 - 167
(2015/12/24)

Synthesis of polysubstituted cyclopenta[b]indoles via relay gold(i)/Bronsted acid catalysis
An efficient relay catalytic process involving Au(i)/Bronsted acid to access various polysubstituted cyclopentannulated indoles from easily accessible 1-(2-aminophenyl)prop-2-ynols and readily available 1,3-dicarbonyls has been developed. In an unprecedented event, the intermediate 2-indolylmethyl cations undergo the cation-Ene reaction with various 1,3-dicarbonyls followed by an intramolecular Friedel-Crafts-type reaction generating functionalized cyclopenta[b]indoles. This journal is
Dhiman, Seema,Ramasastry
p. 557 - 560
(2015/01/09)

A new protocol for nickel-catalysed regio- and stereoselective hydrocyanation of allenes
Regio- and stereoselective hydrocyanation under nickel catalysis is described. This report shows that allenyl C-C double bonds are discriminated and converted to the corresponding carbonitriles as a single product. The key functionalities for achieving high regio- and stereocontrol are aryl and cyclopropyl groups in the substrates. This journal is
Arai, Shigeru,Hori, Hiroto,Amako, Yuka,Nishida, Atsushi
p. 7493 - 7496
(2015/05/04)

NOVEL BENZOAZEPINE DERIVATIVE AND MEDICAL USE THEREOF
A compound having a V2 receptor agonistic activity is provided. Providing a pharmaceutical composition which contains, as an active ingredient, a compound represented by general formula (I) described below: [R1 is formula described below: (A is a lower alkylene group which may be substituted with lower alkyl group; R6 is a hydrogen atom; R7 is a hydroxyl group, an aromatic heterocyclic group which may be substituted with lower alkyl group, carbamoyl group); R2 is a hydrogen atom or lower alkyl group; R3 is lower alkyl group which may be substituted with 1-3 fluorine atoms, or halogen atom; R4 is a five-membered aromatic monocyclic heterocyclic group, five-membered non-aromatic monocyclic heterocyclic group, (provided each heterocyclic groups contain at least one nitrogen atom and may be substituted with a lower alkyl group); and R5 is a lower alkyl group, halogen atom], or pharmacologically acceptable salt thereof.
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(2015/11/18)

A novel protocol for the facile construction of tetrahydroquinoline fused tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction
An efficient method towards the synthesis of quinoline fused tricyclic compounds involving an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction utilizing Baylis-Hillman derivatives in good yields has been described for the first time. A high
Bakthadoss, Manickam,Vinayagam, Varathan
p. 10007 - 10014
(2015/10/12)

Metal-free C-H amination for indole synthesis
An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.
Jang, Young Ho,Youn, So Won
p. 3720 - 3723
(2014/08/05)

Unprecedented synthesis of aza-bridged benzodioxepine derivatives through a tandem Rh(ii)-catalyzed 1,3-rearrangement/[3+2] cycloaddition of carbonyltriazoles
Rh(ii)-catalyzed novel tandem intramolecular cycloisomerizations of aldehydes or ketones with 1-sulfonyl 1,2,3-triazoles have been disclosed, providing a facile protocol to access a series of functionalized aza-bridged benzodioxepine heterocycles.
Zhang, Yong-Sheng,Tang, Xiang-Ying,Shi, Min
p. 15971 - 15974
(2015/01/08)

Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl α,β-unsaturated ketones: Construction of chiral functionalized tetrahydroquinolines
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
p. 5114 - 5121
(2014/07/08)

Asymmetric domino aza-Michael-Michael reaction of o-N-protected aminophenyl α,β-unsaturated ketones: Construction of chiral functionalized tetrahydroquinolines
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
p. 5114 - 5121
(2014/12/10)

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
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
p. 3365 - 3373
(2015/01/09)

RhIII-catalyzed hydroacylation reactions between N-sulfonyl 2-aminobenzaldehydes and olefins
Metal-catalyzed hydroacylation of olefins represents an important atom-economic synthetic process in C-H activation. For the first time highly efficient RhIIICp*-catalyzed hydroacylation was realized in the coupling of N-sulfonyl 2-aminobenzald
Zhang, Tao,Qi, Zisong,Zhang, Xueyun,Wu, Lamei,Li, Xingwei
p. 3283 - 3287
(2014/04/03)

Rhodium(iii)-catalyzed coupling of N-sulfonyl 2-aminobenzaldehydes with oxygenated allylic olefins through C-H activation
Rh(iii)-catalyzed coupling of N-sulfonyl 2-aminobenzaldehydes with oxygenated allylic olefins via C-H bond activation is described. Diarylketones were obtained through coupling of N-sulfonyl 2-aminobenzaldehydes with 7-oxabenzonorbornadienes. On the other
Yang, Tingting,Zhang, Tao,Yang, Shangdong,Chen, Shanshan,Li, Xingwei
p. 4290 - 4294
(2014/06/23)

Highly enantioselective synthesis of chiral 7-ring O- and N-heterocycles by a one-pot nitro-Michael-cyclization tandem reaction
A concise enantioselective approach to synthesise medium-sized 7-ring O- and N-heterocycles has been developed. The synthetic strategy relies on an organocatalytic nitro-Michael-nitrile oxide cycloaddition tandem reaction, leading to the corresponding chiral benzoxe- and benzazepine derivatives containing an additional fused dihydroisoxazoline ring in good yields and excellent enantioselectivities (up to 97% ee).
Rohlmann, Renate,Daniliuc, Constantin-Gabriel,Mancheno, Olga Garcia
supporting information
p. 11665 - 11667
(2013/12/04)