31493-10-4Relevant academic research and scientific papers
Copper-mediated formal [5+1] annulation of 2-vinylanilines and glyoxylic acid: A facile approach for the synthesis of 4-arylated quinolines
Xiang, Yunyu,Luo, Puying,Hao, Tianxin,Xiong, Weikang,Song, Xiaolin,Ding, Qiuping
, (2020/12/13)
A copper-mediated formal [5 + 1] oxidative annulation of 2-vinylanilines and glyoxylic acid to 4-arylated quinolines was developed. A series of 4-arylated quinoline derivatives were obtained in good to excellent yields. This protocol could be carried out efficiently on gram scale. The transformation probably underwent nucleophilic addition/6π electrocyclization/oxidative aromatization and the elimination of CO2 cascade processes.
Direct Assembly of 4-Substituted Quinolines with Vinyl Azides as a Dual Synthon via C=C and C-N Bond Cleavage
Cen, Jinghe,Li, Jianxiao,Zhang, Yu,Zhu, Zhongzhi,Yang, Shaorong,Jiang, Huanfeng
supporting information, p. 4434 - 4438 (2018/08/07)
An unprecedented Zn-promoted selective cleavage of vinyl azides for the synthesis of 4-substituted quinolines is developed. In this conversion, vinyl azides function as a dual synthon via C=C and C-N bond cleavage with two C=C bonds and one C=N bond formation in a one-step manner. The reaction is appreciated for its readily accessible substrates, high step economy, mild conditions, and use of air as the sole oxidant.
Direct Synthesis of Quinolines via Co(III)-Catalyzed and DMSO-Involved C-H Activation/Cyclization of Anilines with Alkynes
Xu, Xuefeng,Yang, Yurong,Zhang, Xu,Yi, Wei
supporting information, p. 566 - 569 (2018/02/10)
A unique Co(III)-catalyzed and DMSO-involved C-H activation/cyclization of simple, cheap, and easily available anilines with alkynes for direct and highly efficient synthesis of privileged quinolines with exclusive regioselectivity and broad substrate/functional group tolerance and in good to excellent yields, where DMSO was employed as both the solvent and the C1 building block of quinoline products, is reported. Mechanistic experiments revealed that the versatile reaction might employ the 2-vinylbenzenamine species as the active intermediate.
The one-pot synthesis of quinolines: Via Co(iii)-catalyzed C-H activation/carbonylation/cyclization of anilines
Xu, Xuefeng,Yang, Yurong,Chen, Xin,Zhang, Xu,Yi, Wei
supporting information, p. 9061 - 9065 (2017/11/14)
We herein disclose a novel Co(iii)-catalyzed C-H activation/carbonylation/cyclization of anilines with ketones using paraformaldehyde as the carbonyl source, giving direct access to diverse quinolines with broad functional group tolerance and in good to excellent yields. Moreover, exclusive site-/region-selectivity was observed in this versatile transformation.
Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines
Yuan, Jin,Yu, Jin-Tao,Jiang, Yan,Cheng, Jiang
, p. 1334 - 1337 (2017/02/15)
A palladium-catalyzed annulation of ortho-vinylanilines with dimethyl sulfoxide was developed to access 4-aryl quinolines in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “=CH-” fragment in this transformation. It represents a facile pathway leading to 4-aryl quinolines.
Iron-catalyzed direct C-H arylation of heterocycles and quinones with arylboronic acids
Deb, Arghya,Manna, Srimanta,Maji, Arun,Dutta, Uttam,Maiti, Debabrata
supporting information, p. 5251 - 5256 (2013/09/02)
The arylation of C-H bonds to generate heteroaryl-aryl (Het-Ar) and arylated quinone (Quin-Ar) compounds has received great attention to achieve sustainable goals in synthetic chemistry. Despite significant advances, arylation of a broad range of Het-Ar and Quin-Ar derivatives remains a challenging task. Herein, a variety of heterocycles are arylated by using arylboronic acids in the presence of catalytic amounts of inexpensive Fe(NO 3)3. The C-arylated quinone compounds can be prepared by reacting arylboronic acids with either quinone or hydroquinone. The present method is operationally simple, scalable, does not require prefunctionalization of the heterocycle or quinone, and can tolerate a wide variety of functional groups in the coupling partners. These qualities are expected to render this method attractive for academic and industrial use. Direct C-H arylation of a variety of heterocycles and quinones with arylboronic acids has been developed. An inexpensive iron catalyst, Fe(NO3)3, and a co-oxidant, persulfate, were used in air. The protocol is applicable for large-scale synthesis and is expected to find application as a result of its operational simplicity. Copyright
