46870-61-5Relevant articles and documents
Method for preparing 2 -arylquinoline from 4 -amino diaryl methanol
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Paragraph 0041-0046, (2021/10/27)
The invention discloses a method for preparing 2 - arylquinoline from 4 -amino diaryl methanol, wherein 2 -aminodiarylmethanol is heated and converted into DMSO arylquinoline compounds under the action of alkali under an oxygen-containing atmosphere in a mixed solution of formaldehyde and 4 . In 4 -arylquinoline compound structure prepared by the method 2-position carbon atoms are provided DMSO, 3-bit carbon atoms are provided by formaldehyde, and all other atoms in the quinoline compound structure are provided by the raw material o-amino aryl methanol. The method for synthesizing 4 - arylquinoline has the advantages of wide raw material sources, environmental friendliness, low price and simple operation, and is beneficial to industrial production.
Time-Resolved EPR Revealed the Formation, Structure, and Reactivity of N -Centered Radicals in an Electrochemical C(sp3)-H Arylation Reaction
Alhumade, Hesham,Gao, Renfei,Huang, Cunlong,Lei, Aiwen,Liu, Yichang,Liu, Zhao,Qi, Xiaotian,Shi, Biyin,Wang, Shengchun
supporting information, p. 20863 - 20872 (2021/12/14)
Electrochemical synthesis has been rapidly developed over the past few years, while a vast majority of the reactions proceed through a radical pathway. Understanding the properties of radical intermediates is crucial in the mechanistic study of electroche
Unexpected Annulation between 2-Aminobenzyl Alcohols and Benzaldehydes in the Presence of DMSO: Regioselective Synthesis of Substituted Quinolines
Yang, Tonglin,Nie, Zhi-Wen,Su, Miao-Dong,Li, Hui,Luo, Wei-Ping,Liu, Qiang,Guo, Can-Cheng
, p. 15228 - 15241 (2021/10/25)
An unexpected annulation among 2-aminobenzyl alcohols, benzaldehydes, and DMSO to quinolines has been disclosed. For the reported annulation between 2-aminobenzyl alcohols and benzaldehydes, the change of the solvent from toluene to DMSO led to the change of the product from the diheteroatomic cyclic benzoxazines to monoheteroatomic cyclic quinolines. This annulation can be used to synthesize regioselectively different substituted quinolines by the choice of different 2-amino alcohols, aldehydes, and sulfoxides as substrates. Interestingly, introducing substituent groups to the α-position of sulfoxides resulted in the interchange of the positions between benzaldehydes and sulfoxides in the product quinolines. On the basis of the control experiments and literatures, a plausible mechanism for this annulation was proposed.
Dearomative Photocatalytic Construction of Bridged 1,3-Diazepanes
Dixon, Darren J.,Duarte, Fernanda,Leitch, Jamie A.,Rogova, Tatiana
supporting information, p. 4121 - 4130 (2020/02/05)
The construction of diverse sp3-rich skeletal ring systems is of importance to drug discovery programmes and natural product synthesis. Herein, we report the photocatalytic construction of 2,7-diazabicyclo[3.2.1]octanes (bridged 1,3-diazepanes) via a reductive diversion of the Minisci reaction. The fused tricyclic product is proposed to form via radical addition to the C4 position of 4-substituted quinoline substrates, with subsequent Hantzsch ester-promoted reduction to a dihydropyridine intermediate which undergoes in situ two-electron ring closure to form the bridged diazepane architecture. A wide scope of N-arylimine and quinoline derivatives was demonstrated and good efficiency was observed in the construction of sterically congested all-carbon quaternary centers. Computational and experimental mechanistic studies provided insights into the reaction mechanism and observed regioselectivity/diastereoselectivity.
Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach
Bartolomeu, Aloisio De A.,Brocksom, Timothy J.,De Oliveira, Kleber T.,No?l, Timothy,Silva, Rodrigo C.
, (2019/08/26)
A metal-free methodology for the photoarylation of pyridines, in water, is described giving 2 and 4-arylated-pyridines in yields up to 96percent. The scope of the aryldiazonium salts is presented showing important results depending on the nature and position of the substituent group in the diazonium salt, that is, electron-donating or electron-withdrawing in the ortho, meta, or para positions. Further heteroaromatics were also successfully photoarylated. Mechanistic studies and comparison between our methodology and similar metal-catalyzed procedures are presented, suggesting the occurrence of a visible-light EDA complex which generates the aryl radical with no need for an additional photocatalyst.
Total syntheses of menisporphine and daurioxoisoporphine c enabled by photoredox-catalyzed direct C-H arylation of isoquinoline with aryldiazonium Salt
Zhang, Jing,Chen, Jie,Zhang, Xiaoyun,Lei, Xiaoguang
, p. 10682 - 10688 (2015/02/19)
Isoquinoline alkaloids are attractive natural products due to their diverse chemical structures as well as remarkable bioactivities. Herein, we report the concise total syntheses of two isoquinoline alkaloids, menisporphine and daurioxoisoporphine C, through a mild and efficient photoredox-catalyzed direct C-H arylation of isoquinoline core with aryldiazonium salt. This new strategy is complementary to the conventional isoquinoline synthesis and would provide us a useful means to achieve a more convergent and flexible approach to access diverse isoquinoline structures.
Synthesis of quinolines from N-tosyl-1-azadienes
Stokes, Sean,Mead, Keith T.
, p. 2627 - 2633 (2013/07/26)
A route to aryl-substituted quinolines from N-tosyl 1-azadienes is described. The key steps are a [4 + 2] cycloaddition with benzyne followed by base treatment of the 1,4-dihydroquinoline product. The N-tosyl 1-azadienes were prepared from readily accessible cinnamaldehyde and chalcone substrates by condensation with p-TsNH2. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
Palladium-catalyzed Suzuki-Miyaura coupling of aryl sulfamates with arylboronic acids
Wang, Zhan-Yong,Ma, Qin-Na,Li, Ren-Hao,Shao, Li-Xiong
, p. 7899 - 7906 (2013/11/19)
Readily available NHC-Pd(ii)-Mp complexes 2 showed efficient catalytic activity toward the Suzuki-Miyaura coupling of aryl sulfamates with arylboronic acids or potassium phenyltrifluoroborate, giving the expected coupling products in good to high yields.
Synthesis of aryl-substituted 1,4-dihydroquinolines by [4+2] cycloaddition of benzyne with 1-azadienes
Stokes, Sean,Bekkam, Markondaiah,Rupp, Madeline,Mead, Keith T.
, p. 389 - 392 (2012/03/12)
The synthesis of aryl-substituted 1,4-dihydroquinolines can be achieved using a [4+2] cycloaddition between benzyne and various aryl-substituted 1-azadienes. The conditions are tolerated by N-aryl-, alkyl-, tosyl-, and tert-butoxycarbonyl-protected 1-azad
Synthesis of substituted quinolines by the electrophilic cyclization of n-(2-alkynyl)anilines
Zhang, Xiaoxia,Yao, Tuanli,Campo, Marino A.,Larock, Richard C.
supporting information; experimental part, p. 1177 - 1187 (2010/04/02)
A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I2, Br2, PhSeBr, and p-O2NC6H4SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the 3-position have been synthesized by the Hg(OTf)2-catalyzed ring closure of these same alkynylanilines.
