Ultrasound-promoted one-pot, four-component synthesis of pyridin-2(1H)-one derivatives

Molecules

Volumn 18, Issue 12, 2013, Pages 14519-14528

  Yang, Jinming ^a,b   Li, Qiang ^c   Zhang, Juanjuan ^b   Lin, Wei ^b   Wang, Juxian ^d   Wang, Yucheng ^d   Huang, Zhibin ^b   Shi, Daqing ^b  

^a YANCHENG TEACHERS UNIVERSITY   (China)

^b SOOCHOW UNIVERSITY   (China)

^c Hainan Chuntch Pharmaceutical Company Limited   (China)

^d INSTITUTE OF MEDICINAL BIOTECHNOLOGY   (China)

Author keywords

Multicomponent reaction; Pyridin 2(1H) one; Ultrasound irradiation

Indexed keywords

PYRIDINE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE; SOUND; SYNTHESIS;

MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRIDINES; SOUND;

EID: 84890934055     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181214519     Document Type: Article

References (31)

1. Nair, V.; Rajesh, C.; Vinod, A.U.; Bindu, S.; Sreekanth, A.R.; Mathen, J.S.; Balagopal, L. Strategies for heterocyclic construction via novel multicomponent reactions based on isocyanides and nucleophilic carbenes. Acc. Chem. Res. 2003, 36, 899-907.
2. Domling, A.; Ugi, I. Multicomponent reactions with isocyanides. Angew. Chem. Int. Ed. 2000, 39, 3168-3210.
3. Domling, A. recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem. Rev. 2006, 106, 17-89.
4. Zhu, J.; Bienaymé, H. Multicomponent Reactions; Wiley-VCH: Weinheim, Germany, 2005; pp. 33-75.
5. Jiang, B.; Tu, S.J.; Kaur, P.; Wever, W.; Li, G. Four-component domino reaction leading to multifunctionalized quinazolines. J. Am. Chem. Soc. 2009, 131, 11660-11661.
6. Sun, J.; Sun, Y.; Xie, Y.J.; Yan, C.G. Facile synthesis of dispirooxindole-fused heterocycles via domino 1,4-dipolar addition and Diels-Alder reaction of in situ generated Huisgen 1,4-dipoles. Org. Lett. 2012, 14, 5172-5175.
7. Li, M.; Cao, H.; Wang, Y.; Lv, X.L.; Wen, L.R. One-pot multicomponent cascade reaction of N,S-ketene acetal: Solvent-free synthesis of imidazo[1,2-a]thiochromeno[3,2-e]pyridines. Org. Lett. 2012, 14, 3470-3473.
8. Feng, X.; Wang, Q.; Lin, W.; Dou, G.L.; Huang, Z.B.; Shi, D.Q. Highly efficient synthesis of polysubstituted pyrroles via four-component domino reaction. Org. Lett. 2013, 15, 2542-2545.
9. Cao, C.P.; Lin, W.; Hu, M.H.; Huang, Z.B.; Shi, D.Q. Highly efficient construction of pentacyclic benzo[b]indeno[1,2,3-de][1,8]naphthyridine derivatives via four-component domino reaction. Chem. Commun. 2013, 49, 6983-6985.
10. Franklin, E.C. Heterocyclic nitrogen compounds. I. Petnacyclic compounds. Chem. Rev. 1935, 16, 305-361.
11. Bergstrom, F.W. Heterocyclic nitrogen compounds. Part IIA. Hexacyclic compounds: Pyridine, quinoline, and isoquinoline. Chem. Rev. 1944, 35, 77-277.
12. Lichtenthaler, F.W. Unsaturated O- and N-heterocycles from carbohydrate feedstocks. Acc. Chem. Res. 2002, 35, 728-737.
13. Dobbin, P.S.; Hider, R.C.; Hall, A.D.; Taylor, P.D.; Sarpong, P.; Porter, J.B. Synthesis, physicochemical properties, and biological evaluation of N-substituted 2-alkyl-3-hydroxy-4(1H)-pyridinones: Orally active iron chelators with clinical potential. J. Med. Chem. 1993, 36, 2448-2458.
14. Rai, B.L.; Dekhordi, L.S.; Khodr, H.; Jin, Y.; Liu, Z.; Hider, R.C. Synthesis, physicochemical properties, and evaluation of N-substituted-2-alkyl- 3-hydroxy-4(1H)-pyridinones. J. Med. Chem. 1998, 41, 3347-3359.
15. Mosti, L.; Schenone, P.; Menozzi, G. Reaction of 2- dimethylaminomethylene-1,3-diones with dinucleophilies. V. Synthesis of 5-acyl-1,2-dihydro-2-oxo-3-pyridinecarbonitriles and 1,2,5,6,7,8-hexahydro-2,5- dioxo-3-quinolinecarboxamides. J. Heterocycl. Chem. 1985, 22, 1503-1509.
16. Mosti, L.; Menozzi, G.; Schenone, P.; Dorigo, P.; Gaion, R.M.; Benetollo, F.; Bombieri, G. Synthesis and cardiotonic activity of esters of 2-substituted 5-cyano-1,6-dihydro-6-oxo-3-pyridinecarboxylic acids. Crystal structure of 2-methyl, 2-t-butyl and 2-phenyl esters. Eur. J. Med. Chem. 1989, 24, 517-529.
17. Nelson, W.O.; Karpishin, T.B.; Rettig, S.J.; Orvig, C. Physical and structural studies of N-substituted-3-hydroxy-2-methyl-4(1H)-pyridinones. Can. J. Chem. 1988, 66, 123-131.
18. Zhang, Z.; Rettig, S.J.; Orvig, C. Lipophilic coordination compounds: Aluminum, gallium, and indium complexs of 1-aryl-3-hydroxy-2-methyl-4- pyridinones. Inorg. Chem. 1991, 30, 509-515.
19. Stoncius, S.; Orentas, E.; Butkus, E.; Ohrstrom, L.; Wendt, O.F.; Wammark, K. An approach to helical tubular self-aggregation using C2-symmetric self-complementary hydrogen-bonding cavity molecules. J. Am. Chem. Soc. 2006, 128, 8272-8285.
20. Cocco, M.T.; Congiu, C.; Onnis, V. Synthesis and antitumour activity of 4-hydroxy-2-pyridone derivatives. Eur. J. Med. Chem. 2000, 35, 545-552.
21. Cocco, M.T.; Congiu, C.; Onnis, V. New bis(pyridyl)methane derivatives from 4-hydroxy-2-pyridones: Synthesis and antitumoral activity. Eur. J. Med. Chem. 2003, 38, 37-47.
22. Cella, R.; Stefani, H.A. Ultrasound in heterocycles chemistry. Tetrahedron 2009, 65, 2619-2641.
23. Cravotto, G.; Cintas, P. Forcing and controlling chemical reactions with ultrasound. Angew. Chem. Int. Ed. 2007, 46, 5476-5478.
24. Li, J.T.; Sun, M.X.; Yin, Y. Ultrasound promoted efficient method for the cleavage of 3-aryl-2,3-epoxyl-1-phenyl-1-propanone with indole. Ultrason. Sonochem. 2010, 17, 359-362.
25. Zou, Y.; Wu, H.; Hu, Y.; Liu, H.; Zhao, X.; Ji, H.L.; Shi, D.Q. A novel and environment-friendly method for preparing dihydropyrano[2,3-c]pyrazoles in water under ultrasound irradiation. Ultrason. Sonochem. 2011, 18, 708-712.
26. Zou, Y.; Hu, Y.; Liu, H.; Shi, D.Q. Rapid and efficient ultrasound-assisted method for the combinatorial synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives. ACS Comb. Sci. 2012, 14, 38-43.
27. Hu, Y.; Zou, Y.; Wu, H.; Shi, D.Q. A facile and efficient ultrasound-assisted synthesis of novel dispiroheterocycles through 1,3-dipolar cycloaddition reactions. Ultrason. Sonochem. 2012, 19, 264-269.
28. Shi, D.Q.; Zou, Y.; Hu, Y.; Wu, H. Imporved synthesis of dihydrothiophenes derivatives under ultrasound irradiation. J. Hetreocycl. Chem. 2011, 48, 896-900.
29. Liu, H.; Zou, Y.; Hu, Y.; Shi, D.Q. An efficient one-pot synthesis of dispiropyrrolidine derivatives through 1,3-dipolar cycloaddition reactions under ultrasound irradiation. J. Heterocycl. Chem. 2011, 48, 877-881.
30. Wang, H.Y.; Zou, Y.; Zhao, X.; Shi, D.Q. A novel and convenient synthesis of 4-hydroxy-6-methyl-3-(1-(phenylimino)ethyl)-2H-pyran-2-one derivatives under ultrasound irradiation. Ultrason. Sonochem. 2011, 18, 1048-1051.
31. Lortente, A.; Galan, C.; Fonseca, I.; Sanz-Aparicio, J. 1-Aminocyclohexene-2,4-dicarbonitrile derivatives. Synthesis and structural study. Can. J. Chem. 1995, 73, 1546-1555.