21075-48-9Relevant academic research and scientific papers
An Oxidant- And Catalyst-Free Synthesis of Dibenzo[ a, c ]carbazoles via UV Light Irradiation of 2,3-Diphenyl-1 H -indoles
Hou, Rong,Kang, Yang,Liang, Yong,Min, Xiaoyan,Wang, Tao,Zhang, Zunting
, (2021/12/13)
An efficient methodology for the synthesis of dibenzo[a,c]- carbazoles via annulation of 2,3-diphenyl-1H-indoles in EtOH under UV light irradiation (λO = 365 nm) along with hydrogen evolution is described. This method exhibits the advantages of mild reaction conditions, no requirement of any oxidants and catalysts, and release of hydrogen as the only byproduct. Notably, the mechanism investigation confirms that the trans-4b,8a-dihydro-9H-dibenzo[a,c]carbazole intermediate could convert into cis-4b,8a-dihydro-9H-dibenzo[a,c]carbazole, which relies on the nitrogen atom of the indole ring. This is followed by intramolecular dehydrogenation which yields the dibenzo[a,c]carbazoles. 2021. Thieme. All rights reserved.
Transition-metal-free, visible-light-mediated cyclization of: O -azidoarylalkynes with aryl diazonium salts
Jin, Cheng,Su, Lianzheng,Ma, Daxi,Cheng, Mingrong
supporting information, p. 14053 - 14056 (2017/11/28)
Visible light along with 3 mol% eosin Y catalyzes the cyclization reaction of o-azidoarylalkynes with aryl diazonium salts by a photoredox process. We have investigated the scope of the reaction for several aryl diazonium salts and o-azidoarylalkynes. The general and easy procedure provides a transition-metal-free alternative for the formation of unsymmetrical 2,3-diaryl-substitued indoles.
Transition-metal-free, visible-light induced cyclization of arylsulfonyl chlorides with o-azidoarylalkynes: a regiospecific route to unsymmetrical 2,3-disubstituted indoles
Gu, Lijun,Jin, Cheng,Wang, Wei,He, Yonghui,Yang, Guangyu,Li, Ganpeng
supporting information, p. 4203 - 4206 (2017/04/21)
A visible-light-catalyzed synthesis of unsymmetrical 2,3-diaryl-substituted indoles from arylsulfonyl chlorides and o-azidoarylalkynes at room temperature has been discovered. This transformation exhibits excellent substrate scope and functional group tolerance. The use of inexpensive eosin Y as the catalyst with easy operation makes this protocol very practical.
Intramolecular addition of diarylmethanols to imines promoted by KO: T -Bu/DMF: A new synthetic approach to indole derivatives
Chen, Jia-Hua,Chen, Zi-Cong,Zhao, Hong,Zhang, Ting,Wang, Wei-Juan,Zou, Yong,Zhang, Xue-Jing,Yan, Ming
, p. 4071 - 4076 (2016/06/14)
KOt-Bu/DMF promoted intramolecular addition of diarylmethanols to imines was developed. A series of 2,3-disubstituted indoles was obtained in good yields. A reaction mechanism of radical cyclization and subsequent dehydration is proposed.
Rhodium-Catalyzed C-H Annulation of Nitrones with Alkynes: A Regiospecific Route to Unsymmetrical 2,3-Diaryl-Substituted Indoles
Yan, Hao,Wang, Haolong,Li, Xincheng,Xin, Xiaoyi,Wang, Chunxiang,Wan, Boshun
, p. 10613 - 10617 (2015/09/02)
The direct C-H annulation of anilines or related compounds with internal alkynes provides straightforward access to 2,3-disubstituted indole products. However, this transformation proceeds with poor regioselectivity in the synthesis of unsymmetrically 2,3-diaryl substituted indoles. Herein, we report the rhodium(III)-catalyzed C-H annulation of nitrones with symmetrical diaryl alkynes as an alternative method to prepare 2,3-diaryl-substituted N-unprotected indoles with two different aryl groups. One of the aryl substituents is derived from N?C-aryl ring of the nitrone and the other from the alkyne substrate, thus providing the indole products with exclusive regioselectivity.
Titanium-Induced Syntheses of Furans, Benzofurans and Indoles
Fuerstner, Alois,Jumbam, Denis N.
, p. 5991 - 6010 (2007/10/02)
Highly reactive titanium on graphite as the reagent of choice promotes intramolecular McMurry type reactions of acyloxy- and acylamido carbonyl compounds affording furans, benzofurans and indoles in good to excellent yields.A variety of reducible groups in the substrates is tolerated (e.g. -F, -Cl, -Br, -I, -CF3, -OMe, -CN, -thiophenyl, -COOR, -CONR2) and strained products such as 11h can be obtained, the X-ray analysis of which is reported.The experimental results indicate the possible formation of dianions from the aromatic aldehydes or ketones as reactive intermediates which attack the ester or amide functions in their proximity, rather than a radical path via ketyls.
