Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-<i>b</i>]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism
The Pot, Atom, and Step Economy (PASE) approach is based on the Pot economy principle and unites it with the Atom and Step Economy strategies; it ensures high efficiency, simplicity and low waste formation. The PASE approach is widely used in multicomponent chemistry. This approach was adopted for t...
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MDPI AG
2020-05-01
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| Series: | Molecules |
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| author | Fedor V. Ryzhkov Yuliya E. Ryzhkova Michail N. Elinson Stepan V. Vorobyev Artem N. Fakhrutdinov Anatoly N. Vereshchagin Mikhail P. Egorov |
| author_facet | Fedor V. Ryzhkov Yuliya E. Ryzhkova Michail N. Elinson Stepan V. Vorobyev Artem N. Fakhrutdinov Anatoly N. Vereshchagin Mikhail P. Egorov |
| author_sort | Fedor V. Ryzhkov |
| collection | DOAJ |
| description | The Pot, Atom, and Step Economy (PASE) approach is based on the Pot economy principle and unites it with the Atom and Step Economy strategies; it ensures high efficiency, simplicity and low waste formation. The PASE approach is widely used in multicomponent chemistry. This approach was adopted for the synthesis of previously unknown hydroxyquinolinone substituted chromeno[2,3-<i>b</i>]pyridines via reaction of salicylaldehydes, malononitrile dimer and hydroxyquinolinone. It was shown that an ethanol-pyridine combination is more beneficial than other inorganic or organic catalysts. Quantum chemical studies showed that chromeno[2,3-<i>b</i>]pyridines has potential for corrosion inhibition. Real time <sup>1</sup>H NMR monitoring was used for the investigation of reaction mechanism and 2-((2<i>H</i>-chromen-3-yl)methylene)malononitrile was defined as a key intermediate in the reaction. |
| first_indexed | 2024-03-10T19:27:29Z |
| format | Article |
| id | doaj.art-2f56e1de571b4ba7a7b1d3c1022d1752 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T19:27:29Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-2f56e1de571b4ba7a7b1d3c1022d17522023-11-20T02:24:29ZengMDPI AGMolecules1420-30492020-05-012511257310.3390/molecules25112573Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-<i>b</i>]pyridines Its Quantum Chemical Study and Investigation of Reaction MechanismFedor V. Ryzhkov0Yuliya E. Ryzhkova1Michail N. Elinson2Stepan V. Vorobyev3Artem N. Fakhrutdinov4Anatoly N. Vereshchagin5Mikhail P. Egorov6N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, RussiaDepartment of Organic Chemistry and Petroleum Chemistry, Gubkin Russian State University of Oil and Gas, 65 Leninsky Prospect, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, RussiaN. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, RussiaThe Pot, Atom, and Step Economy (PASE) approach is based on the Pot economy principle and unites it with the Atom and Step Economy strategies; it ensures high efficiency, simplicity and low waste formation. The PASE approach is widely used in multicomponent chemistry. This approach was adopted for the synthesis of previously unknown hydroxyquinolinone substituted chromeno[2,3-<i>b</i>]pyridines via reaction of salicylaldehydes, malononitrile dimer and hydroxyquinolinone. It was shown that an ethanol-pyridine combination is more beneficial than other inorganic or organic catalysts. Quantum chemical studies showed that chromeno[2,3-<i>b</i>]pyridines has potential for corrosion inhibition. Real time <sup>1</sup>H NMR monitoring was used for the investigation of reaction mechanism and 2-((2<i>H</i>-chromen-3-yl)methylene)malononitrile was defined as a key intermediate in the reaction.https://www.mdpi.com/1420-3049/25/11/2573salicylaldehydemalononitrile dimerhydroxyquinolinonechromeno[2,3-<i>b</i>]pyridinesmulticomponent reactionsPASE approach |
| spellingShingle | Fedor V. Ryzhkov Yuliya E. Ryzhkova Michail N. Elinson Stepan V. Vorobyev Artem N. Fakhrutdinov Anatoly N. Vereshchagin Mikhail P. Egorov Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-<i>b</i>]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism Molecules salicylaldehyde malononitrile dimer hydroxyquinolinone chromeno[2,3-<i>b</i>]pyridines multicomponent reactions PASE approach |
| title | Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-<i>b</i>]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism |
| title_full | Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-<i>b</i>]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism |
| title_fullStr | Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-<i>b</i>]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism |
| title_full_unstemmed | Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-<i>b</i>]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism |
| title_short | Catalyst-Solvent System for PASE Approach to Hydroxyquinolinone-Substituted Chromeno[2,3-<i>b</i>]pyridines Its Quantum Chemical Study and Investigation of Reaction Mechanism |
| title_sort | catalyst solvent system for pase approach to hydroxyquinolinone substituted chromeno 2 3 i b i pyridines its quantum chemical study and investigation of reaction mechanism |
| topic | salicylaldehyde malononitrile dimer hydroxyquinolinone chromeno[2,3-<i>b</i>]pyridines multicomponent reactions PASE approach |
| url | https://www.mdpi.com/1420-3049/25/11/2573 |
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