- Selective Synthesis of Dihydrophenanthridine and Phenanthridine Derivatives from the Cascade Reactions of o-Arylanilines with Alkynoates through C-H/N-H/C-C Bond Cleavage
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In this paper, an unprecedented selective synthesis of dihydrophenanthridine and phenanthridine derivatives through the cascade reactions of 2-arylanilines with alkynoates is presented. Mechanistic studies showed that the formation of the dihydrophenanthr
- Xu, Yuanshuang,Yu, Caiyun,Zhang, Xinying,Fan, Xuesen
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- Methanol as a formylating agent in nitrogen heterocycles
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A radical mediated C-H direct formylation of N-heteroarenes with methanol is reported. The reaction features a novel iron-catalyzed Minisci oxidative coupling process using commercially available methanol as a formylating reagent. It effectively solved the long-standing problems associated with using methanol as a formylating reagent in these types of reactions. Compared to the traditional Minisci C-H formylation methods, this protocol is highly atom-economical, simple to operate, and environmentally friendly and shows good functional group tolerance. This Minisci formylation strategy is a straightforward approach for the late-stage functionalization of N-heteroarenes. This journal is
- Xu, Zhengbao,Zhang, Lizhi
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p. 9476 - 9482
(2021/11/17)
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- Method for selectively synthesizing dihydrophenanthridine or phenanthridine compound
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The invention discloses a method for selectively synthesizing a dihydrophenanthridine compound 3 or a phenanthridine compound 4, and belongs to the technical field of organic synthesis. An o-aryl aniline compound 1 and an acetylenic acid ester compound 2 are used as raw materials, and in the presence of a ruthenium catalyst, an additive and acid, a heating reaction is performed in an organic solvent to obtain a dihydrophenanthridine compound 3 or a phenanthridine compound 4. The method has the following advantages: (1) the synthesis process is simple, and the dihydrophenanthridine or phenanthridine compound can be synthesized with high selectivity by starting from the o-aryl aniline compound and the acetylenic acid ester compound under the catalysis of the ruthenium catalyst and changing the reaction temperature; and (2) the raw materials are cheap and easy to obtain, the reaction conditions are mild, the operation is easy and convenient, and the application range of the substrate is wide.
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Paragraph 0087-0090
(2021/07/01)
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- Photoredox-Catalyzed Redox-Neutral Minisci C?H Formylation of N-Heteroarenes
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We report a protocol for redox-neutral Minisci C?H formylation of N-heteroarenes using 1,3-dioxoisoindolin-2-yl 2,2-diethoxyacetate as a formyl equivalent at room temperature. This scalable benchtop protocol offers a distinct advantage over traditional reductive carbonylation and Minisci C?H formylation methods in not requiring the use of carbon monoxide, pressurized gas, a stoichiometric reductant, or a stoichiometric oxidant. (Figure presented.).
- Dong, Jianyang,Wang, Xiaochen,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
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supporting information
p. 2155 - 2159
(2020/02/11)
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- Copper-catalyzed three-component reaction of: N-heteroaryl aldehydes, nitriles, and water
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An efficient and straightforward method for the synthesis of N-heteroaroyl imides has been successfully developed involving a copper-catalyzed radical-triggered three-component reaction of N-heteroaryl aldehydes, nitriles, and water. Mechanistic studies indicate that the reaction may undergo a radical-triggered Ritter-type reaction in which water serves as the oxygen source for the formation of the C-O bond. The reaction has advantages such as a broad substrate scope for the N-heteroaryl aldehydes, atom economy, and simple operation.
- Bao, Hanyang,Zhou, Bingwei,Jin, Hongwei,Liu, Yunkui
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p. 5021 - 5028
(2019/06/03)
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- Method for synthesizing 6-aldehyde phenanthridine compound and derivatives thereof
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The invention provides a method for synthesizing a 6-aldehyde phenanthridine compound. The method is as below: using a substituted azide terminal alkene compound represented by a formula I as a starting material, conducting a reaction using acetonitrile or a mixed solvent of acetonitrile and water as a reaction solvent under the action of an oxidizing agent at 60 to 100 DEG C for 6 to 12 hours, and conducting post-treatment on the obtained reaction solution to obtain the 6-aldehyde phenanthridine compound represented by a formula II and derivatives thereof. The mass ratio of the substituted azide terminal alkene compound represented by the formula I and the oxidizing agent is 1:(1-3); and the oxidizing agent is a mixture of one or more selected from the group comprising iodobenzene diacetate, t-butyl hydroperoxide and potassium persulfate. The method of the invention is safe and environmentally friendly, and does not generate waste gas or wastewater; the substrate has good adaptability, a variety of substituents can be aromatized, and an aldehyde group is formed; the reaction condition is mild; and the reaction can be carried out at a lower temperature.
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Paragraph 0023-0034
(2019/03/26)
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- Photoredox-Catalyzed Decarboxylative C-H Acylation of Heteroarenes
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A mild, environmentally friendly, and regioselective acylation of heterocycles with inexpensive carboxylic acids is reported via photoredox catalysis. The strategy is highlighted with good functional group tolerance and substrate scope which could rapidly
- Jia, Wei,Jian, Yong,Huang, Binbin,Yang, Chao,Xia, Wujiong
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supporting information
p. 1881 - 1886
(2018/08/28)
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- Hydrolytically stable chemiluminescent labels and their conjugates, and assays therefrom
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A novel chemiluminescent labeling compositions comprising an ester, thioester or amide covalently and jointly bonded to (1) a carbon of a heterocyclic ring or ring system that is susceptible to attack by peroxide or molecular oxygen and (2) an aryl ring or ring system wherein the heterocyclic ring or ring system is distinguished by a heteroatom thereof in an oxidation state which causes the attacked carbon atom to form an intermediate that decays and produces chemiluminescence; the aryl ring or ring system contains at least three substituents on a six-member aromatic hydrocarbon that together sterically and electronically hinder hydrolysis of the linkage, which substituents involve ortho substituent groups on the aryl in conjunction with meta and/or para substituents thereon that possess an electron withdrawing capacity characterized as a ?p value greater than 0 and less than 1. Included are the chemiluminescent labeling composition conjugated with a specific binding material; a chemiluminescent assay comprising the conjugate; and a chemiluminescent assay kit comprising the conjugate with the capability of conducting the assay.
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- Nitro substituted chemiluminescent labels and their conjugates, and assays therefrom
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A novel chemiluminescent labeling compositions comprising an ester, thiolester or amide covalently and jointly bonded to (1) a carbon of a heterocyclic ring or ring system that is susceptible to attack by peroxide or molecular oxygen and (2) an aryl ring
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- SYNTHESE DANS LA SERIE DES PHENANTHRIDINES. IV. PREPARATION DE NOUVEAUX RADIOPROTECTEURS A MOTIF PHENANTHRIDINE
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New phenanthridines substituted in the 6-position by a β-aminoethylthiol chain have been synthesized.These new products are easily obtained from 6-methylphenanthridine by a Mannich reaction or from 6-bromophenanthridine by substitution.From the 6-carboxaldehydophenanthridine and the β-aminoethylthiol, the corresponding thiazolidine or imine are obtained.These compounds are likely to be new radioprotectors.
- Lion, Claude,Boukou-Poba, Jean-Paul,Charvy, Claude
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p. 169 - 174
(2007/10/02)
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