European Journal of Chemistry

Ecofriendly and simple synthesis of pyrano[3,2-c]quinolone in water via an efficient one-pot three-component reaction

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Published: Mar 31, 2018
DOI: https://doi.org/10.5155/eurjchem.9.1.44-48.1679
Keywords:
Ethanolamine, One pot reaction, Pyranoquinolinone, 4-Hydroxyquinolinone, Multicomponent reaction, Cinnamonitrile derivatives
Section
Research Article
Issue
Vol. 9 No. 1 (2018): March 2018
Dates
Received 2017-12-28
Accepted 2018-01-25
Published 2018-03-31
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Ibrahim Ali Radini
Chemistry Department, Faculty of Science, Jazan University, Jazan, 2079, Kingdom of Saudi Arabia
https://orcid.org/0000-0003-2835-4874
Sameh Ramadan El-Gogary
Chemistry Department, Faculty of Science, Damietta University, New Damietta, 34518, Egypt
https://orcid.org/0000-0002-0465-4023
Mohamed Sabri Mostafa
Chemistry Department, Faculty of Science, Jazan University, Jazan, 2079, Kingdom of Saudi Arabia
https://orcid.org/0000-0003-3537-3598
Bander Alnagei
Chemistry Department, Faculty of Science, Jazan University, Jazan, 2079, Kingdom of Saudi Arabia
https://orcid.org/0000-0001-5513-7838
Mohammed Mudarbish
Chemistry Department, Faculty of Science, Jazan University, Jazan, 2079, Kingdom of Saudi Arabia
https://orcid.org/0000-0002-5754-4995
Shadad Dash
Chemistry Department, Faculty of Science, Jazan University, Jazan, 2079, Kingdom of Saudi Arabia
https://orcid.org/0000-0002-2602-0080

Abstract

Pyrano[3,2-c]quinolones are commonly found in alkaloids, manifesting diverse biological activities. In this work, 2-amino-6-methyl-5-oxo-4-substituted-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitriles and ethyl 2-amino-4-(substituted)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylates have been synthesized efficiently from reaction of 4-hydroxy-1-methylquinolin-2(1H)-one, aldehydes and active methylene nitriles in one-pot three component reaction in aqueous medium, containing catalytic amount of ethanolamine resulting in 70-95% yields.


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Radini, I. A.; El-Gogary, S. R.; Mostafa, M. S.; Alnagei, B.; Mudarbish, M.; Dash, S. Ecofriendly and Simple Synthesis of pyrano[3,2-c]quinolone in Water via an Efficient One-Pot Three-Component Reaction. Eur. J. Chem. 2018, 9, 44-48.

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References

[1]. Asghari, S.; Ramezani, S.; Mohseni, M. Chin. Chem. Lett. 2014, 25, 431-434.
https://doi.org/10.1016/j.cclet.2013.12.010

[2]. Hassanin, H.; Ibrahim, M.; Alnamer, Y. Turk. J. Chem. 2012, 36, 682-699.

[3]. Fujita, Y.; Oguri, H.; Oikawa, H. J. Antibiot. 2005, 58, 425-427.
https://doi.org/10.1038/ja.2005.56

[4]. Chen, J. J.; Chen, P. H.; Liao, C. H.; Huang, S. Y.; Chen, I. S. J. Nat. Prod. 2007, 70, 1444-1448.
https://doi.org/10.1021/np070186g

[5]. Isaka, M.; Tanticharoen, M.; Kongsaeree, P.; Thebtaranonth, Y. J. Org. Chem. 2001, 66, 4803-4808.
https://doi.org/10.1021/jo0100906

[6]. Magedov, V.; Madhuri, M.; Marcia, O.; Adriana, D.; Snezna, R.; Severine, V.; Wim, S.; Nikolai, E.; Pavel, U.; Eerik, E.; Erica, K.; Paul, T.; Mikhail, A.; Alexander, K. J. Med. Chem. 2008, 51(8), 2561-2570.
https://doi.org/10.1021/jm701499n

[7]. Kamperdick, C.; Van, N. H.; Van Sung, T.; Adam, G. Phytochemistry 1999, 50, 177-181.
https://doi.org/10.1016/S0031-9422(98)00500-7

[8]. Chen, I. S.; Wu, S. J.; Tsai, I. L.; Wu, T. S.; Pezzuto, J. M.; Lu, C.; Chai, H.; Suh, N.; Teng, M. J. Nat. Prod. 1994, 57, 1206-1211.
https://doi.org/10.1021/np50111a003

[9]. Heiner, E. Molecules 2012, 17, 1074-1102.
https://doi.org/10.3390/molecules17011074

[10]. Bhupathi, R.; Madhu, B.; Devi, R.; Reddy, R.; Dubey, K. J. Heterocycl. Chem. 2016, 53(6), 1911-1916.
https://doi.org/10.1002/jhet.2506

[11]. Shehata, A. S.; Faida, H.; Moustafa, M. A.; Mashaly, M. M. J. Am. Sci. 2011, 7(11), 240-242.

[12]. Kumar, N. V.; Rajendran, S. P. Heterocycl. Commun. 2004, 10, 289-294.

[13]. Dodia, N.; Shah, A. Heterocycl. Commun. 2001, 7, 289-294.
https://doi.org/10.1515/HC.2001.7.3.289

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