196872-91-0Relevant academic research and scientific papers
Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines
Liu, Yan,Li, Shi-Jun,Chen, Xiao-Lan,Fan, Lu-Lu,Li, Xiao-Yun,Zhu, Shan-Shan,Qu, Ling-Bo,Yu, Bing
, p. 688 - 694 (2020/01/02)
A Mn(III)-mediated radical cyclization reaction of o-vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2-functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6-endo-trig radical cyclization of o-vinylaryl isocyanides, giving a number of structurally unique and biologically potential 2-functionalized quinoline derivatives.
One-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed three-component cascade annulation of amines, alkyne esters and terminal alkynes
Li, Yunlan,Zhang, Qiurui,Xu, Xuefeng,Zhang, Xu,Yang, Yurong,Yi, Wei
supporting information, p. 965 - 970 (2019/03/13)
Described herein is a new and general method for one-pot synthesis of 2,4-disubstituted quinolines via silver-catalyzed [3 + 1 + 2] annulation of simple amines, alkyne esters and terminal alkynes. The versatile transformation might initiate with the facil
Manganese(ii)-catalysed dehydrogenative annulation involving C-C bond formation: highly regioselective synthesis of quinolines
Wang, Chengniu,Yang, Jinfei,Meng, Xiao,Sun, Yufeng,Man, Xuyan,Li, Jinxia,Sun, Fei
supporting information, p. 4474 - 4478 (2019/04/05)
An inexpensive nontoxic manganese(ii)-catalysed dehydrogenative annulation was developed for C-C bond formation. The reaction showed high selectivity and efficiency across a broad substrate scope. Remarkably simple conditions and the ability to conduct gram-scale synthesis underscore this method's utility. To demonstrate the potential of this approach, we tested the drug effects of compound 3n, which showed activity for blocking vascular development. The results of this study will be important for the treatment of eye diseases and tumors caused by vascular proliferation.
Establishing the correlation between catalytic performance and N→Sb donor-acceptor interaction: Systematic assessment of azastibocine halide derivatives as water tolerant Lewis acids
Lei, Jian,Peng, Lingteng,Qiu, Renhua,Liu, Yongping,Chen, Yi,Au, Chak-Tong,Yin, Shuang-Feng
, p. 8478 - 8487 (2019/06/19)
A series of organoantimony(iii) halide complexes with a tetrahydrodibenzo[c,f][1,5]azastibocine framework were synthesized and employed as water tolerant Lewis acid catalysts. The results of a systematic structure-activity relationship study demonstrated that the strength of N→Sb donor-acceptor interaction could be synergistically modulated by tuning the properties of the nitrogen substituents and halogen atoms adjacent to the central antimony atom, and consequently resulted in distinct catalytic performances towards organic reactions such as Mannich, cross-condensation, cyclization-aromatization and epoxide aminolysis reaction. The fluorinated organoantimony(iii) derivatives were found to be more active than those of the chlorinated, brominated and iodinated analogues, owing to the use of an Sb-F moiety as a hydrogen bond acceptor. By comparison, the compound 6-cyclohexyl-12-fluoro-5,6,7,12-tetrahydrodibenzo[c,f][1,5] azastibocine (1d) is found to exhibit the highest catalytic activity, together with facile reusability in scale enlarged synthesis.
Microwave-Assisted Metal-Free Rapid Synthesis of C4-Arylated Quinolines via Povarov Type Multicomponent Reaction
Chandra, Devesh,Dhiman, Ankit Kumar,Kumar, Rakesh,Sharma, Upendra
, p. 2753 - 2758 (2019/04/08)
A rapid microwave assisted, (±) camphor-10-sulfonic acid (CSA) promoted, Povarov type multicomponent synthesis of 4-arylated quinolines from anilines, alkynes, and paraformaldehyde is described. This reaction proceeds through [4+2] cycloaddition of imine (formed in situ from aniline and paraformaldehyde) and alkynes in the presence of CSA, without any metal catalyst. Mechanistic study revealed that CSA inhibit the synthesis of Troger's base and assist the cycloaddition of imines with alkynes by activating the imine.
Method for constructing quinoline compound by means of functionalization of organic antimony catalyzed C-H bond
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Paragraph 0090; 0091, (2017/08/29)
The invention aims at developing a novel method for preparing a quinoline compound in a manner of high conversion rate and high yield from organic antimony frustrated lewis pair catalyst by means of C-H bond functionalization of imine and unsaturated hydr
A method for the synthesis of quinoline derivatives
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Paragraph 0055-0058, (2017/08/23)
The invention belongs to the technical field of organic synthesis and particularly relates to a synthesis method of quinoline derivatives. The synthesis method comprises the steps of sequentially adding aromatic amine, aldehyde and alcohol into a reaction
Mechanistic Insights into the B(C6F5)3-Initiated Aldehyde-Aniline-Alkyne Reaction to Form Substituted Quinolines
Fasano, Valerio,Radcliffe, James E.,Ingleson, Michael J.
supporting information, p. 1623 - 1629 (2017/04/28)
A substoichiometric quantity of the Lewis acid B(C6F5)3 is sufficient to initiate the aldehyde-amine-alkyne reaction, in a one-pot methodology that enables the synthesis of a range of functionalized quinolines. Optimization studies revealed that key requirements for the high-yielding tricomponent reaction initiated by B(C6F5)3 at raised temperatures include an excess of the in situ generated imine (which acts as a hydrogen acceptor) and an alkyne substituent able to stabilize positive charge buildup during the cyclization. Mechanistic experiments revealed that under these conditions B(C6F5)3 is acting as a Lewis acid-assisted Br?nsted acid, with H2O-B(C6F5)3 being the key species enabling catalytic quinoline formation. This was indicated by deuterium labeling studies and the observation that the cyclization of N-(3-phenylpropargyl)aniline using B(C6F5)3 under anhydrous conditions afforded the zwitterion [(N-H-3-B(C6F5)3-4-Ph-quinolinium], which does not undergo protodeboronation to release B(C6F5)3 and the quinoline product under a range of conditions. Finally, a brief substrate scope exploration demonstrated that this is an operationally simple and effective methodology for the production of functionalized quinolines.
Rare-earth metal chlorides catalyzed one-pot syntheses of quinolines under solvent-free microwave irradiation conditions
Zhang, Lijun,Wu, Bing,Zhou, Yongqing,Xia, Jing,Zhou, Shuangliu,Wang, Shaowu
, p. 465 - 471 (2013/08/25)
Under microwave irradiation and solvent-free conditions, rare-earth metal chlorides (RECl3) have been efficient catalysts for one-pot synthesis of quinoline derivatives to give products in good to excellent yields through the multi-component reactions of aldehydes, amines, and alkynes. The rare-earth metal chlorides can be recycled for six times without notable loss of catalytic activities. This new synthetic approach has prominent features of a short reaction time, high yields of products, operational simplicity, broad substrate scopes, environmentally friendly property and commercially available catalysts. It extends the applications of rare-earth metal compounds as catalysts in organic synthesis. A convenient method for the syntheses of quinoline derivatives through multi-component reactions of aldehydes, amines, and alkynes in the presence of rare-earth metal chlorides as catalysts under microwave irradiation and solvent-free conditions was developed.
An efficient synthesis of substituted quinolines via indium(III) chloride catalyzed reaction of imines with alkynes
Zhu, Mei,Fu, Weijun,Xun, Chen,Zou, Guanglong
experimental part, p. 43 - 47 (2012/03/10)
An efficient synthetic method for the preparation of quinolines through indium(III) chloride-catalyzed tandem addition-cyclization-oxidation reactions of imines with alkynes was developed. The processes can provide a diverse range of quinoline derivatives
