Iron/acetic acid mediated intermolecular tandem C–C and C–N bond formation: an easy access to acridinone and quinoline derivatives

RSC Advances ◽  
2014 ◽  
Vol 4 (71) ◽  
pp. 37806-37811 ◽  
Author(s):  
R. R. Rajawinslin ◽  
Sachin D. Gawande ◽  
Veerababurao Kavala ◽  
Yi-Hsiang Huang ◽  
Chun-Wei Kuo ◽  
...  

An efficient iron/acetic acid mediated one pot reductive cyclization protocol was successfully developed for the synthesis of acridinone and quinoline derivatives.

ChemInform ◽  
2015 ◽  
Vol 46 (11) ◽  
pp. no-no
Author(s):  
R. R. Rajawinslin ◽  
Sachin D. Gawande ◽  
Veerababurao Kavala ◽  
Yi-Hsiang Huang ◽  
Chun-Wei Kuo ◽  
...  

Synthesis ◽  
2017 ◽  
Vol 50 (06) ◽  
pp. 1350-1358 ◽  
Author(s):  
Cunde Wang ◽  
Xushun Qing ◽  
Ting Wang ◽  
Chenlu Dai ◽  
Zhenjie Su

An efficient iron/acetic acid system-mediated reductive cyclization reaction of substituted 2-aryl-3-nitro-2H-chromenes with substituted 2-nitrobenzaldehydes for the synthesis of 6-aryl-6H-chromeno[3,4-b]quinolines was developed. This reaction involves the sequential reduction, hydrolysis, aldol condensation, intramolecular addition, and the nucleophilic addition of substituted 2-aryl-3-nitro-2H-chromenes with substituted 2-nitrobenzaldehydes to give the corresponding 6H-chromeno[3,4-b]quinolines. This transformation provides a straightforward synthetic protocol for constructing substituted 6H-chromeno[3,4-b]quinoline derivatives. The structures of three typical products were confirmed by X-ray crystallography.


2018 ◽  
Vol 47 (10) ◽  
pp. 3239-3242 ◽  
Author(s):  
Jing Tong ◽  
Tingting Xu ◽  
Shengjun Liu ◽  
Junxiang Zhang ◽  
Xudong Hou ◽  
...  

Ti-based cage of [Ti4O2L4Cl8] (L = 4-acetamidobenzoic acid) is synthesized by a one-pot solvothermal reaction of the 4-aminobenzoic acid, acetic acid and TiCl4. Ti(iv) ion functions as a Lewis acid catalyst and coordination sites to afford Ti-based cage formation in a cascade fashion.


2020 ◽  
Vol 7 (1) ◽  
pp. 23-39 ◽  
Author(s):  
Kantharaju Kamanna ◽  
Santosh Y. Khatavi

Multi-Component Reactions (MCRs) have emerged as an excellent tool in organic chemistry for the synthesis of various bioactive molecules. Among these, one-pot MCRs are included, in which organic reactants react with domino in a single-step process. This has become an alternative platform for the organic chemists, because of their simple operation, less purification methods, no side product and faster reaction time. One of the important applications of the MCRs can be drawn in carbon- carbon (C-C) and carbon-heteroatom (C-X; X = N, O, S) bond formation, which is extensively used by the organic chemists to generate bioactive or useful material synthesis. Some of the key carbon- carbon bond forming reactions are Grignard, Wittig, Enolate alkylation, Aldol, Claisen condensation, Michael and more organic reactions. Alternatively, carbon-heteroatoms containing C-N, C-O, and C-S bond are also found more important and present in various heterocyclic compounds, which are of biological, pharmaceutical, and material interest. Thus, there is a clear scope for the discovery and development of cleaner reaction, faster reaction rate, atom economy and efficient one-pot synthesis for sustainable production of diverse and structurally complex organic molecules. Reactions that required hours to run completely in a conventional method can now be carried out within minutes. Thus, the application of microwave (MW) radiation in organic synthesis has become more promising considerable amount in resource-friendly and eco-friendly processes. The technique of microwaveassisted organic synthesis (MAOS) has successfully been employed in various material syntheses, such as transition metal-catalyzed cross-coupling, dipolar cycloaddition reaction, biomolecule synthesis, polymer formation, and the nanoparticle synthesis. The application of the microwave-technique in carbon-carbon and carbon-heteroatom bond formations via MCRs with major reported literature examples are discussed in this review.


2017 ◽  
Vol 28 (6) ◽  
pp. e21408 ◽  
Author(s):  
Samia Guezane-Lakoud ◽  
Martial Toffano ◽  
Louisa Aribi-Zouioueche

ChemInform ◽  
2015 ◽  
Vol 46 (17) ◽  
pp. no-no
Author(s):  
Wen-Ming Shu ◽  
Jun-Rui Ma ◽  
Kai-Lu Zheng ◽  
Hui-Ying Sun ◽  
Mei Wang ◽  
...  

2018 ◽  
Vol 90 (4) ◽  
pp. 607-616
Author(s):  
Yin-Ping Wang ◽  
Yue-Jian Lin ◽  
Guo-Xin Jin

AbstractFor the first time, carborane complexes containing a B(4)–S bond were obtained directly by heating mononuclear Pd-B(4)-bound carborane complexes. A possible mechanism involved in sulfur atom migration is presented in which the leaving group, pyridine, benzyl isocyanide or PPh3, is demonstrated to be the trigger of the reaction process. In this work, efficient routes are developed through one-pot reactions to prepare B(4)-S carborane derivatives.


2015 ◽  
Vol 11 ◽  
pp. 1163-1174 ◽  
Author(s):  
Michael Weßling ◽  
Hans J Schäfer

Nitroalkenes are easily accessible in high variety by condensation of aldehydes with aliphatic nitroalkanes. They belong to the group of activated alkenes that can be hydrodimerized by cathodic reduction. There are many olefins with different electron withdrawing groups used for cathodic hydrodimerization, but not much is known about the behaviour of the nitro group. Synthetic applications of this group could profit from the easy access to nitroolefins in large variety, the C–C bond formation with the introduction of two nitro groups in a 1,4-distance and the conversions of the nitro group by reduction to oximes and amines, the conversion into aldehydes and ketones via the Nef reaction and base catalyzed condensations at the acidic CH bond. Eight 1-aryl-2-nitro-1-propenes have been electrolyzed in an undivided electrolysis cell to afford 2,5-dinitro-3,4-diaryl hexanes in high yield. The 4-methoxy-, 4-trifluoromethyl-, 2-chloro- and 2,6-difluorophenyl group and furthermore the 2-furyl and 2-pyrrolyl group have been applied. The reaction is chemoselective as only the double bond but not the nitro group undergoes reaction, is regioselective as a ß,ß-coupling with regard to the nitro group and forms preferentially two out of six possible diastereomers as major products.


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