Xi:Irritant;
52488-36-5Relevant articles and documents
Superhydrophobic nickel/carbon core-shell nanocomposites for the hydrogen transfer reactions of nitrobenzene and N-heterocycles
Duan, Zhiying,Liu, Fangfang,Pang, Shaofeng,Su, Qiong,Wang, Yanbin,Xie, Xin,Zhang, Ping,Zhang, Yujing,Zhou, Feng
, p. 1996 - 2010 (2020/04/07)
In this work, catalytic hydrogen transfer as an effective, green, convenient and economical strategy is for the first time used to synthesize anilines and N-heterocyclic aromatic compounds from nitrobenzene and N-heterocycles in one step. Nevertheless, how to effectively reduce the possible effects of water on the catalyst by removal of the by-product water, and to further introduce water as the solvent based on green chemistry are still challenges. Since the structures and properties of carbon nanocomposites are easily modified by controllable construction, a one step pyrolysis process is used for controllable construction of micro/nano hierarchical carbon nanocomposites with core-shell structures and magnetic separation performance. Using various characterization methods and model reactions the relationship between the structure of Ni?NCFs (nickel-nitrogen-doped carbon frameworks) and catalytic performance was investigated, and the results show that there is a positive correlation between the catalytic performance and hydrophobicity of catalysts. Besides, the possible catalytically active sites, which are formed by the interaction of pyridinic N and graphitic N in the structure of nitrogen-doped graphene with the surfaces of Ni nanoparticles, should be pivotal to achieving the relatively high catalytic performance of materials. Due to its unique structure, the obtained Ni?NCF-700 catalyst with superhydrophobicity shows extraordinary performances toward the hydrogen transfer reaction of nitrobenzene and N-heterocycles in the aqueous state; meanwhile, it was also found that Ni?NCF-700 still retained its excellent catalytic activity and structural integrity after three cycles. Compared with traditional catalytic systems, our catalytic systems offer a highly effective, green and economical alternative for nitrobenzene and N-heterocycle transformation, and may open up a new avenue for simple construction of structure and activity defined carbon nanocomposite heterogeneous catalysts with superhydrophobicity.
Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid
Beaudry, Christopher M.,Points, Gary L.,Stout, Kenneth T.
supporting information, p. 16655 - 16658 (2020/12/01)
A Diels–Alder reaction-based strategy for the synthesis of indoles and related heterocycles is reported. An intramolecular cycloaddition of alkyne-tethered 3-aminopyrones gives 4-substituted indolines in good yield and with complete regioselectivity. Additional substitution is readily tolerated in the transformation, allowing synthesis of complex and non-canonical substitution patterns. Oxidative conditions give the corresponding indoles. The strategy also allows the synthesis of carbazoles. The method was showcased in a formal synthesis of lysergic acid.
DMSO/t-BuONa/O2-Mediated Aerobic Dehydrogenation of Saturated N-Heterocycles
Cai, Hu,Tan, Wei,Xie, Yongfa,Yang, Ruchun,Yue, Shusheng
, p. 7501 - 7509 (2020/07/07)
Aromatic N-heterocycles such as quinolines, isoquinolines, and indolines are synthesized via sodium tert-butoxide-promoted oxidative dehydrogenation of the saturated heterocycles in DMSO solution. This reaction proceeds under mild reaction conditions and has a good functional group tolerance. Mechanistic studies suggest a radical pathway involving hydrogen abstraction of dimsyl radicals from the N-H bond or α-C-H of the substrates and subsequent oxidation of the nitrogen or α-aminoalkyl radicals.
A indole compound and its preparation method and application (by machine translation)
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Paragraph 0131; 0138; 0139, (2018/10/02)
The invention discloses a indole compound and its preparation method and application. The indole compounds of the structural formula such as formula (I) is shown. The indoles, rice galenical demonstrate the excellent inhibitory activity, the effect of most of the compound is obviously better than the positive control drug validamycin; especially compound I - 43, I - 44, I - 54, I - 73, II - 7 and II - 17, its galenical very good living body protection and treating effect, effect is better than the positive control; more specifically, compound I - 43 of the rice sheath blight bacteriostatic activity than validamycin activity is improved by nearly 300 times. The indole compounds in the prevention and/or treatment of rice sheath blight has great application prospects. In addition the compound of the invention is simple in construction, the preparation method is simple, and is suitable for large-scale industrial production. (I). (by machine translation)
Dehydrogenation of Nitrogen Heterocycles Using Graphene Oxide as a Versatile Metal-Free Catalyst under Air
Zhang, Jingyu,Chen, Shiya,Chen, Fangfang,Xu, Wensheng,Deng, Guo-Jun,Gong, Hang
supporting information, p. 2358 - 2363 (2017/07/22)
Graphene oxide (GO) has been developed as an inexpensive, environmental friendly, metal-free carbocatalyst for the dehydrogenation of nitrogen heterocycles. Valuable compounds, such as quinoline, 3,4-dihydroisoquinoline, quinazoline, and indole derivatives, have been successfully used as substrates. The investigation of various oxygen-containing molecules with different conjugated systems indicated that both the oxygen-containing groups and large π-conjugated system in GO sheets are essential for this reaction. (Figure presented.).
Half-sandwich structured ruthenium complex and preparation method thereof, and method for reducing o-nitrobenzene ethanol compound into indole compound
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Paragraph 0080; 0087, (2017/07/22)
The invention discloses a half-sandwich structured ruthenium complex and a preparation method thereof, and a method for reducing an o-nitrobenzene ethanol compound into an indole compound. The structure of the ruthenium complex is as shown in formula (A), wherein in the formula (A), X is halogen, R is H, -oxyl, halogen or nitro, and n is a positive integer ranging from 1 to 4. By the adoption of the preparation method, the ruthenium complex with excellent chemical stability can be obtained; meanwhile, the preparation method has the advantages of simple operation, low equipment requirement and batch production; furthermore, the ruthenium complex can be used as a catalyst for catalytically reducing the o-nitrobenzene ethanol compound (Refer to Specification).
4 - bromo - 2 - hydroxy indole synthesis method (by machine translation)
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Paragraph 0062; 0068, (2017/04/27)
The present invention provides 4 - bromo - 2 - hydroxy indole synthesis method, its steps are as follows: (1) the aluminum powder and zirconium oxide grinding ball into the ball mill pot ball grinding pre-processing aluminum powder; (2) hydrogenation the sodium uses pentane is pretreated pre-processing sodium hydride; (3) the pre-processing of aluminum powder and pretreatment sodium hydride, zirconium oxide grinding ball, to join the ball rubs the pot ball grindingnitric acid titanium, products of sodium aluminum hydride; (4) there will be aluminum nitrate, nitrate by the sol - gel process compound indium catalyst; (5) the α - (N, N - dimethylamino) - 2 - bromo - 6 nitrobenzene ethylene for the cyclization catalyst reduction compound indium prepared 4 - bromo indole; (6) the 4 - bromo indole with oxalyl, methanol prepared through the reaction of 4 - bromo indole - 2 - carboxylic acid; (7) will be 4 - bromo indole - 2 - carboxylic acid is sodium aluminum hydride reduction to obtain the target product. The invention of high yield, low cost. (by machine translation)
Dehydrogenative N-heterocyclization of 2-(2-aminoaryl)ethyl alcohols to indole derivatives catalyzed by (μ-oxo)tetraruthenium cluster/1,2- bis(diphenylphosphino)benzene
Kondo, Teruyuki,Kanda, Takashi,Takagi, Daisuke,Wada, Kenji,Kimura,Toshimitsu, Akio
, p. 1015 - 1022 (2013/08/15)
A novel catalyst system of (μ-oxo)tetraruthenium cluster (2) combined with 1,2-bis(diphenylphosphino)benzene (dppbz) realized a simple, selective, and practical synthesis of indole and its derivatives from 2-(2-aminoaryl)ethyl alcohols via dehydrogenative N-heterocyclization reaction. Spontaneous formation of a stoichiometric amount of hydrogen (H2) was observed, and the present reaction proceeded smoothly under an argon atmosphere without oxidants and/or hydrogen acceptors.
A systematic study of two complementary protocols allowing the general, mild and efficient deprotection of N-pivaloylindoles
Ruiz, Míriam,Sánchez, J. Domingo,López-Alvarado, Pilar,Menéndez, J. Carlos
experimental part, p. 705 - 710 (2012/01/06)
Two mild and general protocols for the high-yielding deprotection of indoles and related fused heterocyclic systems are described, involving either hydride transfer from LDA or hydrolysis by the DBU-water system. Both methods were shown to tolerate a wide variety of substituents and functional groups, but the hydrolytic one proved to be particularly general, being compatible with 2-alkyl substituents, aldehydes, ketones, carboxylic acids, halogens, ethers, amides and esters. Yields were normally excellent in both cases, but were usually slightly higher for the reductive method. Taken together, these two protocols provide a general solution to the problem of pivaloyindole deprotection.
Enantioselective N-H functionalization of indoles with α,β- unsaturated γ-lactams catalyzed by chiral Bronsted acids
Xie, Yinjun,Zhao, Yingwei,Qian, Bo,Yang, Lei,Xia, Chungu,Huang, Hanmin
supporting information; experimental part, p. 5682 - 5686 (2011/08/03)
Nitrogen revives: Cyclic N-acyliminium ions were generated from α,β-unsaturated γ-lactams (1) and underwent intermolecular addition by indole nucleophiles (2) under the catalysis of a chiral Bronsted acid (3). A variety of N-functionalized indole derivatives containing a pyrrolidinone moiety (4) were assembled with high enantioselectivity. Bn=benzyl. Copyright
