Efficient one-pot synthesis of 2-amino-4H-chromenes catalyzed by ferric hydrogen sulfate and Zr-based catalysts of FI

Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry

Volumn 41, Issue 9, 2011, Pages 1067-1073

  Eshghi, H ^a   Damavandi, S ^a   Zohuri, G H ^a  

^a FERDOWSI UNIVERSITY OF MASHHAD   (Iran)

Author keywords

Amino 4H chromenes; Ferric hydrogen sulfate; Threecomponent condensation

Indexed keywords

EID: 84855776320     PISSN: 15533174     EISSN: 15533182     Source Type: Journal    
DOI: 10.1080/15533174.2011.591347     Document Type: Article

References (23)

1. Montgomery, J. Nickel-catalyzed cyclizations couplings, and cycloadditions involving three reactive components. Acc. Chem. Res. 2000, 33, 467-473.
2. Chen, L.; Huang, X.-J.; Li, Y.-Q.; Zheng, W.-J. A one-pot multicomponent reaction for the synthesis of 2-amino-2-chromenes promoted by N,Ndimethylamino- functionalized basic ionic liquid catalysis under solventfree condition. Monatsh. Chem. 2009, 140, 45-47.
3. Mohr, S.J.; Chirigos,M.A.; Fuhrman, F.S.; Pryor, J.W. Pyran copolymer as an effective adjuvant to chemotherapy against a murine leukemia and solid tumor. Cancer Res. 1975, 35, 3750.
4. Kumar, A.; Sharma, S.; Maurya, R.A.; Sarkar, J. Diversity oriented synthesis of benzoxanthene and benzochromene libraries via one-pot, threecomponent reactions and their anti-proliferative activity. J. Comb. Chem. 2010, 12, 20-24.
5. Bonsignore, L.; Loy, G.; Secci, D.; Calignano, A. Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives. Eur. J. Med. Chem. 1993, 28, 517-520. (Pubitemid 23200215)
6. Bianchi, G.; Tava, A. Synthesis of (2R)-(+)-2, 3-Dihydro-2, 6-dimethyl- 4H-pyran-4-one, a homologue of pheromones of a species in the Hepialidae family. Agric. Biol. Chem. 1987, 51, 2001.
7. Anderson, D.R.; Hegde, S.; Reinhard, E.; Gomez, L.; Vernier, W.F.; Lee, L.; Liu, S.; Sambandam, A.; Snider, P.A.; Masih, L. Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2). Bioorg. Med. Chem. Lett. 2005, 15, 1587-1590. (Pubitemid 40312534)
8. Tarik, A.; Magdy, I.; Somaia, A. Synthesis of biologically active 4-oxo-4Hchromene derivatives containing sulfur-nitrogen heterocycles. Phosphorus Sulfur Silicon 2009, 184, 2358-2392.
9. Kemnitzer, W.; Drewe, J.; Jiang, S.; Zhang, H.; Wang, Y.; Zhao, J.; Jia, S.; Herich, J.; Labreque, D.; Storer, R.; Meerovitch, K.; Bouffard, D.; Rej, R.; Denis, R.; Blais, C.; Lamothe, S.; Attardo, G.; Gourdeau, H.; Tseng, B.; Kasibhatla, S.; Cai, S.X. J. Med. Chem. 2004, 47, 6299-6304.
10. Dyachenko, V.D.; Chernega, A.N. Aliphatic aldehydes in multicoponent syntheses of 4-alkyl substituted partially hydrogenated quinolines, fused 4H-pyrans, and 2-amino-4-ethyl-5-methylbenzene-1,3- dicarbonitrile. Russ. J. Org. Chem. 2006, 42, 567-576. (Pubitemid 43760653)
11. Ballini, R.; Bosica, G.; Conforti, M.L.; Maggi, R.; Mazzacanni, A.; Righi, P.; Sartori, G. Three-component process for the synthesis of 2-amino-2- chromenes in aqueous media. Tetrahedron 2001, 57, 1395-1398. (Pubitemid 32150051)
12. Rong, L.; Li, X.; Wang H.; Shi, D.; Tu, S.; Zhuang Q. Efficient green procedure for the Knoevenagel condensation under solvent-free conditions. Synth. Commun. 2006, 36, 2407-2412. (Pubitemid 44266694)
13. Maggi, R.; Ballini, R.; Sartori, G.; Sartorio, R. Basic alumina catalysed synthesis of substituted 2-amino-2-chromenes via three-component reaction. Tetrahedron Lett. 2004, 45, 2297.
14. Heravi,M.M.; Baghernejad,B.; Oskooie, H.A.Anovel and efficient catalyst to one-pot synthesis of 2-amino-4H-chromenes by methanesulfonic acid. J. Chin. Chem. Soc. 2008, 55, 3-7.
15. Kidwai, M.; Saxena, S.; Khan, M.K.R.; Thukral, S.S. Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents. Bioorg. Med. Chem. Lett. 2005, 15, 4295-4298. (Pubitemid 41188006)
16. Kumar, A.; Sharma, S.; Maurya, R.A.; Sarkar, J. Diversity oriented synthesis of benzoxanthene and benzochromene libraries via one-pot, threecomponent reactions and their anti-proliferative activity. J. Comb. Chem. 2010, 12, 20-24.
17. Zhou, D.; Ren, Z.; Cao, W.; Chena, J.; Deng H. Solvent-free one-pot approach for synthesis of substituted 2-aminochromenes. J. Heterocyclic Chem. 2008, 45, 1865-1867.
18. Mandar, P.; Surpur, S.K.; Shriniwas D.S. Exploitation of the catalytic efficacy of Mg/Al hydrotalcite for the rapid synthesis of 2-aminochromene derivatives via a multicomponent strategy in the presence of microwaves. Tetrahedron Lett. 2009, 50, 719-722.
19. Jin, T.S.H.; Xiao, J.C.H.; Wang, S.J.; Li, T.S.H. Ultrasound-assisted synthesis of 2-amino-2-chromenes with cetyltrimethylammonium bromide in aqueous media. Ultrason. Sonochem. 2004, 11, 393-397.
20. Eshghi, H.; Hassankhani,A. Regioselective synthesis of e-oximes catalyzed by ferric chloride under solvent free conditions. Org. Prep. Proced. Int. 2005, 37, 575-582.
21. Eshghi, H. Ferric hydrogensulfate catalysed schmidt reaction of ketones to amides under solvent-free conditions. J Chin. Chem. Soc. 2006, 53, 987-990.
22. Makarem, S.; Mohammadi, A.A.; Fakhari; A.R. A multi-component electro-organic synthesis of 2-amino-4H-chromenes Tetrahedron Lett. 2008, 49, 7194-7198.
23. Ahmadjo, S.; Zohuri, G.H.; Damavandi, S.; Sandaroos, R. Comparative ethylene polymerization using FI-like zirconium based catalysts. Reaction Kinet. Mech. Catal. 2010, 101, 429-442.