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The Development of Friedländer Heteroannulation Through a Single Electron Transfer and Energy Transfer Pathway Using Methylene Blue (MB)

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Journal Sci Rep
Specialty Science
Date 2022 May 4
PMID 35508509
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Abstract

The radical Friedländer hetero-annulation of 2-aminoaryl ketone and -methylene carbonyl compound was used to develop a green tandem approach for the metal-free synthesis of polysubstitutedquinolines. At room temperature in an ethanol solvent, photo-excited state functions generated from MB were used as single-electron transfer (SET) and energy transfer (EnT) catalysts, utilizing visible light as a renewable energy source in the air atmosphere. The purpose of this research is to increase the use of a nonmetal cationic dye that is both inexpensive and widely available. High yields, energy-effectiveness, high atom economy, time-saving features of the reaction, and operational simplicity, and the least amount of a catalyst are the benefits of this study. As a result, a wide range of ecological and long-term chemical properties are obtained. Polysubstitutedquinolines' turnover number (TON) and turnover frequency (TOF) have been calculated. Surprisingly, such cyclization can be accomplished on a gram scale, indicating that the process has industrial potential.

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References
1.
Maayani S, Weinstein H, Ben-Zvi N, Cohen S, Sokolovsky M . Psychotomimetics as anticholinergic agents. I. 1-Cyclohexylpiperidine derivatives: anticholinesterase activity and antagonistic activity to acetylcholine. Biochem Pharmacol. 1974; 23(8):1263-81. DOI: 10.1016/0006-2952(74)90330-x. View

2.
Lekhok K, Bhuyan D, Prajapati D, Boruah R . Zinc triflate: a highly efficient reusable catalyst in the synthesis of functionalized quinolines via Friedlander annulation. Mol Divers. 2009; 14(4):841-6. DOI: 10.1007/s11030-009-9214-0. View

3.
Srivastava S, Chauhan P, Bhaduri A, Fatima N, Chatterjee R . Quinolones: novel probes in antifilarial chemotheraphy. J Med Chem. 2000; 43(11):2275-9. DOI: 10.1021/jm990438d. View

4.
Verschueren R, De Borggraeve W . Electrochemistry and Photoredox Catalysis: A Comparative Evaluation in Organic Synthesis. Molecules. 2019; 24(11). PMC: 6600520. DOI: 10.3390/molecules24112122. View

5.
Kidwai M, Bhushan K, Sapra P, Saxena R, Gupta R . Alumina-supported synthesis of antibacterial quinolines using microwaves. Bioorg Med Chem. 2000; 8(1):69-72. DOI: 10.1016/s0968-0896(99)00256-4. View