- Enantio- and Diastereoselective, Complete Hydrogenation of Benzofurans by Cascade Catalysis
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We report an enantio- and diastereoselective, complete hydrogenation of multiply substituted benzofurans in a one-pot cascade catalysis. The developed protocol facilitates the controlled installation of up to six new defined stereocenters and produces architecturally complex octahydrobenzofurans, prevalent in many bioactive molecules. A unique match of a chiral homogeneous ruthenium-N-heterocyclic carbene complex and an in situ activated rhodium catalyst from a complex precursor act in sequence to enable the presented process.
- Gallagher, Timothy,Glorius, Frank,Hu, Tianjiao,Moock, Daniel,Wagener, Tobias
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supporting information
p. 13677 - 13681
(2021/05/10)
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- THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION
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Disclosed herein are compounds of formula I: or a salt thereof and compositions comprising a compound of formula I or a pharmaceutically acceptable salt thereof. Also disclosed herein are methods for treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I or a pharmaceutically acceptable salt thereof, alone or in combination with a bacterial efflux pump inhibitor.
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Paragraph 0446-0447
(2019/02/13)
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- Direct Dimesitylborylation of Benzofuran Derivatives by an Iridium-Catalyzed C?H Activation with Silyldimesitylborane
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Direct dimesitylborylation of benzofuran derivatives by a C?H activation catalyzed by an iridium(I)/N-heterocyclic carbene (NHC) complex in the presence of Ph2MeSi-BMes2 afforded the corresponding dimesitylborylation products in good to high yield with excellent regioselectivity. This method provides a straightforward route to donor–(π-spacer)–acceptor systems with intriguing solvatochromic luminescence properties.
- Shishido, Ryosuke,Sasaki, Ikuo,Seki, Tomohiro,Ishiyama, Tatsuo,Ito, Hajime
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supporting information
p. 12924 - 12928
(2019/11/05)
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- Biocatalytic Strategy for Highly Diastereo- and Enantioselective Synthesis of 2,3-Dihydrobenzofuran-Based Tricyclic Scaffolds
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2,3-Dihydrobenzofurans are key pharmacophores in many natural and synthetic bioactive molecules. A biocatalytic strategy is reported here for the highly diastereo- and enantioselective construction of stereochemically rich 2,3-dihydrobenzofurans in high enantiopurity (>99.9% de and ee), high yields, and on a preparative scale via benzofuran cyclopropanation with engineered myoglobins. Computational and structure-reactivity studies provide insights into the mechanism of this reaction, enabling the elaboration of a stereochemical model that can rationalize the high stereoselectivity of the biocatalyst. This information was leveraged to implement a highly stereoselective route to a drug molecule and a tricyclic scaffold featuring five stereogenic centers via a single-enzyme transformation. This work expands the biocatalytic toolbox for asymmetric C–C bond transformations and should prove useful for further development of metalloprotein catalysts for abiotic carbene transfer reactions.
- Vargas, David A.,Khade, Rahul L.,Zhang, Yong,Fasan, Rudi
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supporting information
p. 10148 - 10152
(2019/07/04)
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- Dioxazolones as masked ester surrogates in the Pd(ii)-catalyzed direct C-H arylation of 6,5-fused heterocycles
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A simple and effective Pd(ii)-catalyzed regioselective C(2)-H arylation of 6,5-fused heterocycles with dioxazolones as a masked ester surrogate under mild conditions is reported. The significance of the arylation is highlighted by the new reactivity demonstrated in dioxazolones via proximal C-H activation of the cyclic carbonate of the hydroxamic acid functionality under protic conditions.
- Saxena, Paridhi,Maida, Neha,Kapur, Manmohan
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supporting information
p. 11187 - 11190
(2019/09/30)
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- Metal- and Reagent-Free Anodic C?C Cross-Coupling of Phenols with Benzofurans leading to a Furan Metathesis
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Heterobiaryls consisting of a phenol and a benzofuran motif are of significant importance for pharmaceutical applications. An attractive sustainable, metal- and reagent-free, electrosynthetic, and highly efficient method, that allows access to (2-hydroxyphenyl)benzofurans is presented. Upon the electrochemical dehydrogenative C?C cross-coupling reaction, a metathesis of the benzo moiety at the benzofuran occurs. This gives rise to a substitution pattern at the hydroxyphenyl moiety which would not be compatible by a direct coupling process. The single-step protocol is easy to conduct in an undivided electrolysis cell, therefore scalable, and inherently safe.
- Lips, Sebastian,Frontana-Uribe, Bernardo Antonio,D?rr, Maurice,Schollmeyer, Dieter,Franke, Robert,Waldvogel, Siegfried R.
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supporting information
p. 6057 - 6061
(2018/03/27)
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- Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N′-Acyl Arylhydrazines
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A novel ligand-free palladium-catalyzed C-2 arylation of benzofurans has been developed using N′-acyl arylhydrazines as the coupling partners and TEMPO as an oxidant. This protocol features a wide functional-group tolerance and highly regioselective products with good to excellent yields.
- Cao, Jun,Chen, Zi-Li,Li, Shu-Min,Zhu, Gao-Feng,Yang, Yuan-Yong,Wang, Cong,Chen, Wen-Zhang,Wang, Jian-Ta,Zhang, Ji-Quan,Tang, Lei
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supporting information
p. 2774 - 2779
(2018/06/21)
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- Copper-Catalyzed Ring Opening of Benzofurans and an Enantioselective Hydroamination Cascade
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A copper(II) acetate/(R)-DTBM-SEGPHOS-catalyzed ring opening of benzofurans and enantioselective hydroamination cascade with dimethoxymethylsilane (DMMS) and hydroxylamine esters is described. Starting from readily available substituted benzofurans, a series of chiral N,N-dibenzylaminophenols, which are of high interest in pharmaceutical chemistry, were obtained with excellent enantioselectivities (up to 66 % yield, 94 % ee).
- Xu-Xu, Qing-Feng,Liu, Qiang-Qiang,Zhang, Xiao,You, Shu-Li
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supporting information
p. 15204 - 15208
(2018/10/24)
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- C-benzo five-membered heteroaromatic aryl glucoside derivative as well as preparation method and application thereof
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The invention discloses a C-benzo five-membered heteroaromatic aryl glucoside derivative shown in the general formula (I) (in the description), a preparation method of the derivative or an intermediate of the derivative, as well as application of the derivative. In the general formula (I), R, R1, R2, R3, R4, X and Y are defined in the description. The C-benzo five-membered heteroaromatic aryl glucoside derivative is novel in structure, has quite strong inhibitory activity on SGLT-2, has high selection ratio for SGLT-1 and SGLT-2, and can be used for preparing drugs for treating and preventing diseases relevant to SGLT-2.
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Paragraph 0146; 0147
(2016/10/08)
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- OXADIAZINE COMPOUNDS AND METHODS OF USE THEREOF
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The present disclosure relates to oxadiazine compounds, pharmaceutical compositions comprising an effective amount of an oxadiazine compound and methods for using an oxadiazine compound in the treatment of a neurodegenerative disease, comprising administering to a subject in need thereof an effective amount of an oxadiazine compound.
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Paragraph 0206
(2016/12/26)
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- Palladium-Catalyzed Dearomatizing Difunctionalization of Indoles and Benzofurans
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A palladium-catalyzed dearomatizing difunctionalization of N-Boc-indoles and benzofurans to give tricyclic indolines and 2,3-dihydrobenzofurans with a fully substituted carbon center is described. Product formation occurs under mild conditions at room temperature with commercially available aryl boronic acids and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) as a mild oxidant in good yields. 2-Carboxyalkyl-substituted indoles and benzofurans react under Pd-catalysis with aryl boronic acids and TEMPO through dearomatizing arylation/cyclization to the corresponding indolines and dihydrobenzofurans containing a lactone moiety bearing a fully substituted carbon center.
- Ramella, Vincenzo,He, Zhiheng,Daniliuc, Constantin G.,Studer, Armido
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supporting information
p. 2268 - 2273
(2016/05/19)
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- Visible light-induced monofluoromethylenation of heteroarenes with ethyl bromofluoroacetate
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Visible light-induced monofluoromethylenation of benzofurans and benzothiophenes with ethyl bromofluoroacetate was developed. This method provided a convenient access to novel α-fluoro-α-heteroarylesters under mild reaction conditions.
- Yu, Wei,Xu, Xiu-Hua,Qing, Feng-Ling
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supporting information
p. 6564 - 6567
(2016/08/09)
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- A Pincer Ruthenium Complex for Regioselective C-H Silylation of Heteroarenes
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A pincer Ru(II) catalyst for the highly efficient undirected silylation of O- and S-heteroarenes with (TMSO)2MeSiH and Et3SiH is described, producing heteroarylsilanes with exclusive C2-regioselectivity, good functional-group tolerance, and high turnover numbers (up to 1960). The synthetic utility of the silylated products is demonstrated by Pd-catalyzed Hiyama-Denmark cross-coupling under mild conditions. One-pot, two-step silylation and coupling procedures have been also developed.
- Fang, Huaquan,Guo, Le,Zhang, Yuxuan,Yao, Wubing,Huang, Zheng
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supporting information
p. 5624 - 5627
(2016/11/17)
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- Zeolite-catalyzed synthesis of 2,3-unsubstituted benzo[b]furans via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals
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An efficient and environmentally benign heterogeneous catalytic process for the synthesis of 2,3-unsubstituted benzo[b]furans has been established via the intramolecular cyclization of 2-aryloxyacetaldehyde acetals. By utilizing tin-exchanged H-β zeolite (Sn-β) as catalyst, a wide range of functionalized 2,3-unsubstituted benzo[b]furans could be prepared in good to excellent yields. The Sn-β zeolite catalyst also exhibited excellent shape selectivity on the cyclization of meta-substituted 2-aryloxyacetaldehyde acetals, and 6-substituted isomers were preferably formed up to 97% regio-selectivity. Moreover, Sn-β zeolite could be easily recovered and reused without any noticeable activity loss.
- Sun, Nan,Huang, Peng,Wang, Yifan,Mo, Weimin,Hu, Baoxiang,Shen, Zhenlu,Hu, Xinquan
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supporting information
p. 4835 - 4841
(2015/07/27)
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- The synthesis of some new hydrazone derivatives containing the benzothiazole moiety
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Hydrazones are an important class of compounds found in many synthetic products. Due to their importance in synthetic chemistry, the present article reports the synthesis of a new series of ten compounds based on the coupling of 2-oxo-3(2H)-benzothiazoleacetic acid, hydrazide and 2-thioxo-3(2H)- -benzothiazoleacetic acid, hydrazide with different aldehydes. The structures of the synthesized compounds were confirmed by elemental analyses, IR, 1H- -NMR, 13C-NMR and FAB+-MS spectral data. Copyright 2012 (CC) SCS.
- Oezdemir, Ahmet,Turan-Zitouni, Guelhan,Kaplancikli, Zafer Asim,Altintop, Mehlika Dilek
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scheme or table
p. 141 - 146
(2012/06/18)
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- Piperidine derivative rennin inhibitors
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Disclosed are piperidine derivatives, their manufacture and use as inhibitors of renin.
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Page/Page column 18
(2010/02/08)
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- PREPARATION AND CYCLIZATION OF ARYLOXYACETALDEHYDE ACETALS; A GENERAL SYNTHESIS OF 2,3-UNSUBSTITUTED BENZOFURANS
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A improved method for the preparation of 2,3-unsubstituted benzofurans is described.Specifically, the PPA catalysed cyclization of aryloxyacetaldehyde acetals to give (4-7)-substituted benzofurans has been achieved.
- Barker, Peter,Finke, Paul,Thompson, Kevan
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p. 257 - 266
(2007/10/02)
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- Bronchodilator and Antiulcer Phenoxypyrimidinones
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Series of 5-phenoxy-2(1H)-pyrimidinones, 5-phenoxy-4(3H)-pyrimidinones, and related compounds were prepared in a follow-up of a lead prepared as a potential cyclic nucleotide regulating agent.Compounds were evaluated for bronchodilator activity in histamine-challenged guinea pigs and for antiulcer activity in a cold-restraint, stressed rat ulcer model.Bronchodilator activity comparable to, or greater than, that of theophylline was found in both the 2(1H)- and 4(3H)-pyrimidinone series and was most prominent in analogues containing either an electron-withdrawing or -donating substituent in the para position of the phenoxy ring.Significant antiulcer activity was observed only in the 2(1H)-pyrimidinone series among three closely related analogues.One of these, 5-(m-methylphenoxy)-2(1H)-pyrimidinone (3), exhibited more potent antiulcer effects than the clinically useful antiulcer agent carbenoxolone, without demonstrating bronchodilator activity.
- Lipinski, C. A.,Stam, J. G.,Pereira, J. N.,Ackerman, N. R.,Hess, H.-J.
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p. 1026 - 1031
(2007/10/02)
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- Reactions of 1,2- and 1,3-amino-alcohols with imidate salts and with ortho esters
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ω-Hydroxy-N-substituted amidines have been shown to be the intermediates in the formation of 2-oxazolines and 5,6-dihydro-4H-1,3-oxazines from the reactions of imidates and 1,2- and 1,3-amino-alcohols respectively, 1,2- and 1,3-Amino-alcohols also react with ortho esters to give 2-oxazolines and 5,6-dihydro-4H-1,3-oxazines, but N-acylamino-alcohols give rise to oxazolidines with ortho esters.
- Butt, Mohammed I.,Neilson, Douglas G.,Watson, Kathleen M.,Zakir-Ullah
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p. 2328 - 2332
(2007/10/04)
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