- Microwave assisted rapid synthesis of phenoxazines and benzopyridoxazines
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A facile protocol for the synthesis of phenoxazines and benzopyridoxazines by Smiles rearrangement have been demonstrated in short reaction time under microwave irradiation. The control experiments suggest that a reaction proceeds through Smiles rearrangement followed SNAr ring closure by in situ cascade process. In our present work, both the electron donating and electron withdrawing groups were tolerant and provided a corresponding phenoxazine/benzopyridoxazine in good to moderate yields.
- Anchan, Kavitha,Puttappa, Nagaswarupa H.,Poongavanam, Baburajan,Sarkar, Sujit Kumar
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supporting information
p. 635 - 646
(2020/11/27)
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- Pyrazinamide compounds, preparation method and application thereof as well as bactericide
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The invention relates to the field of pesticide bactericides and discloses pyrazinamide compounds, a preparation method and an application thereof as well as a bactericide. The compounds have the structure shown in formula (I). The pyrazinamide compounds with the novel structure are designed by introducing pyrazine ring fragments in Pyradiflumid and diphenyl ether fragments with wide bioactivity,and the pyrazinamide compounds can be used as novel SDHIs (succinate dehydrogenase inhibitors) or bactericides.
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Paragraph 0140-0143
(2018/06/04)
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- Csp2-Csp2 and Csp2-N Bond Formation in a One-Pot Reaction between N-Tosylhydrazones and Bromonitrobenzenes: An Unexpected Cyclization to Substituted Indole Derivatives
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A novel, sequential, palladium-catalyzed, cross-coupling reaction using N-tosylhydrazone and bromonitrobenzene derivatives followed by reductive cyclization has been developed. This transformation providing an efficient route to unexpected N-arylindole derivatives involves, in a one-pot reaction, the formation of one Csp2-Csp2 bond and two Csp2-N bonds together with the cleavage of one Csp2-heteroatom bond. Evaluation of the biological activity led to the identification of compound 5a, which displays potent activity at nanomolar concentrations against human colon carcinoma cell line.
- Bzeih, Tourin,Lamaa, Diana,Frison, Gilles,Hachem, Ali,Jaber, Nada,Bignon, Jerome,Retailleau, Pascal,Alami, Mouad,Hamze, Abdallah
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supporting information
p. 6700 - 6703
(2017/12/26)
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- Access to Chiral Seven-Member Cyclic Amines via Rh-Catalyzed Asymmetric Hydrogenation
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A highly efficient asymmetric hydrogenation of azepine/oxazepine-type seven-member cyclic imine hydrochlorides was successfully developed using Rh/bisphosphine-thiourea ligand ZhaoPhos, affording various chiral seven-member cyclic amines with full conversions, high yields, and excellent enantioselectivities (up to 96% yield, >99% ee). Additionally, this asymmetric hydrogenation can proceed well on gram scale with excellent ee value. Moreover, control experimental results displayed that the anion-bonding interaction between the chloride ion of the substrate and thiourea motif of the ZhaoPhos played an important role to obtain excellent enantioselectivity.
- Li, Pan,Huang, Yi,Hu, Xinquan,Dong, Xiu-Qin,Zhang, Xumu
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supporting information
p. 3855 - 3858
(2017/07/26)
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- An efficient domino Sonogashira/double carbopalladation/C-H-activation reaction leading to fluorescent polycyclic aromatic hydrocarbons
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A facile synthesis of fluorescent polycyclic aromatic hydrocarbons through a highly productive palladium-catalyzed fourfold domino Sonogashira/double carbopalladation/C-H-activation process was developed.
- Tietze, Lutz F.,Eichhorst, Christoph
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p. 919 - 927
(2015/05/27)
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- Palladium-Catalyzed Synthesis of Six-Membered Benzofuzed Phosphacycles via Carbon-Phosphorus Bond Cleavage
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The palladium-catalyzed synthesis of dibenzofused six-membered phosphacycles via carbon-phosphorus bond cleavage is developed. This method is compatible with a range of functional groups, such as esters, amides, and carbamates, which is in sharp contrast to the limitations of the classical method using organolithium reagents. (Figure Presented).
- Baba, Katsuaki,Tobisu, Mamoru,Chatani, Naoto
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supporting information
p. 70 - 73
(2015/07/28)
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- Transition-metal-free intramolecular N-arylations
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N-Substituted phenoxazines and related aza analogs have been prepared from N-acetylated aryloxy anilides by transition-metal-free, base-catalyzed cyclization reactions. In the presence of a mixture of 10 mol % of N,N′-dimethylethylenediamine (DMEDA) and 2 equiv of K2CO 3 in toluene at 135 °C the products are obtained in high yields.
- Thome, Isabelle,Bolm, Carsten
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supporting information; experimental part
p. 1892 - 1895
(2012/05/20)
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- Synthesis and enantioselective hydrogenation of seven-membered cyclic imines: Substituted dibenzo[b,f][1,4]oxazepines
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Highly enantioselective hydrogenation of seven-membered cyclic imines, substituted dibenzo[b,f][1,4]oxazepines, was achieved, with up to 94% ee, by using the [Ir(COD)Cl]2/(S)-Xyl-C3*-TunePhos complex as the catalyst in the presence of morpholine-HCl.
- Gao, Kai,Yu, Chang-Bin,Li, Wei,Zhou, Yong-Gui,Zhang, Xumu
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supporting information; experimental part
p. 7845 - 7847
(2011/09/13)
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- One-pot Synthesis of Dibenzofurans via SNAr and Subsequent Ligand-free Palladium-catalyzed Intramolecular Aryl-aryl Cross-coupling Reactions under Microwave Irradiation
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An efficient one-pot synthesis of dibenzofurans, via SNAr reaction of aryl halides and ortho-bromophenols in the presence of anhydrous K2CO 3 and subsequent ligand-free palladium-catalyzed intramolecular aryl-aryl cross-coupling cyclization under microwave irradiation, is described.
- Che, Zhiping,Xu, Hui
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experimental part
p. 833 - 836
(2011/10/05)
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- Synthesis of dibenzofurans directly from aryl halides and ortho-bromophenols via one-pot consecutive SNAr and intramolecular palladium-catalyzed aryl-aryl coupling reactions
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A series of dibenzofurans were efficiently and conveniently synthesized via one-pot consecutive C(sp2)-O bond formation reaction (SNAr) in the presence of anhydrous K2CO3, followed by C(sp 2)-C(sp2) b
- Xu, Hui,Fan, Ling-Ling
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experimental part
p. 1496 - 1498
(2009/10/16)
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- Catalytic activation of silylated nucleophiles using tBu-P4 as a base
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Trialkylsilyl groups play an important role as effective protecting groups in organic synthesis. Various O, N, and C nucleophilic sites can be protected by trialkylsilyl groups to control the selectivity of reactions. The nucleophilic attack of a fluoride anion on a silyl group is recognized as one of the most useful methods for desilylation. The activation of the nucleophile-silicon bond is important not only for desilylation but also for the generation of a reactive nucleophilic anion to achieve a new bond formation. The phosphazene bases developed by Schwesinger are known to be strong non-metallic organic bases. Among them, the tBu-P4 base has been used for various selective deprotonative transformations, although the ability of tBu-P4 base to activate silylated nucleophiles has not yet been shown. A novel catalytic activation of various O, N, and C nucleophile-silicon bonds using tBu-P4 base was investigated to perform nucleophilic reactions with various electrophiles. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.
- Ueno, Masahiro,Hori, Chieko,Suzawa, Koichi,Ebisawa, Masashi,Kondo, Yoshinori
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p. 1965 - 1968
(2007/10/03)
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- Arylmethanesulfonates are convenient latent phenols in the nucleophilic aromatic substitution reaction
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The methanesulfonyl protecting group for a phenol is conveniently unmasked under the conditions of the S(N)Ar reaction with an activated aryl halide, producing diarylether products directly. The method is advantageous when the preparation of a phenol substrate requires O-protection, since the selection of the robust methanesulfonate as a latent phenol obviates a deprotection step prior to the S(N)Ar reaction.
- Dinsmore, Christopher J.,Zartman, C. Blair
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p. 3989 - 3990
(2007/10/03)
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- The Reduction of Some 2,2'-Dinitrodiaryl Compounds and Related Compounds by Thiourea S,S-Dioxide (Formamidinesulfinic Acid)
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The reaction of thiourea S,S-dioxide (formamidinesulfinic acid) in ethanolic alkali with 2,2'-dinitrobiphenyl and several related dinitro compounds possessing an-X-bridge (where X = NH, NMe, O and S), located at the 1,1'-positions, has been investigated.With 2,2'-dinitrobiphenyl (which gives good yields of benzocinnoline and its oxides) and, to a minor extent, with 2,2'-dinitrodiphenylamine, an intramolecular reaction occured to give heterocyclic products; with each of the other dinitro compounds, the only product obtained was formed as the result of a Smiles rearrangement.
- Wilshire, John F. K.
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p. 995 - 1001
(2007/10/02)
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