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Original Articles

Efficient One-Pot Synthesis of 2-Amino-4H-chromenes Catalyzed by Ferric Hydrogen Sulfate and Zr-Based Catalysts of FI

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Pages 1067-1073 | Received 16 Mar 2011, Accepted 05 Apr 2011, Published online: 07 Nov 2011

REFERENCES

  • Montgomery , J. 2000 . Nickel-catalyzed cyclizations couplings, and cycloadditions involving three reactive components . Acc. Chem. Res. , 33 : 467 – 473 .
  • Chen , L. , Huang , X.-J. , Li , Y.-Q. and Zheng , W.-J. 2009 . A one-pot multicomponent reaction for the synthesis of 2-amino-2-chromenes promoted by N,N-dimethylamino-functionalized basic ionic liquid catalysis under solvent-free condition. . Monatsh. Chem , 140 : 45 – 47 .
  • Mohr , S. J. , Chirigos , M. A. , Fuhrman , F. S. and Pryor , J. W. 1975 . Pyran copolymer as an effective adjuvant to chemotherapy against a murine leukemia and solid tumor . Cancer Res. , 35 : 3750
  • Kumar , A. , Sharma , S. , Maurya , R. A. and Sarkar , J. 2010 . Diversity oriented synthesis of benzoxanthene and benzochromene libraries via one-pot, three-component reactions and their anti-proliferative activity . J. Comb. Chem , 12 : 20 – 24 .
  • Bonsignore , L. , Loy , G. , Secci , D. and Calignano , A. 1993 . Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives . Eur. J. Med. Chem , 28 : 517 – 520 .
  • Bianchi , G. and Tava , A. 1987 . 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 , 51 : 2001
  • Anderson , D. R. , Hegde , S. , Reinhard , E. , Gomez , L. , Vernier , W. F. , Lee , L. , Liu , S. , Sambandam , A. , Snider , P. A. and Masih , L. 2005 . Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2) . Bioorg. Med. Chem. Lett , 15 : 1587 – 1590 .
  • Tarik , A. , Magdy , I. and Somaia , A. 2009 . Synthesis of biologically active 4-oxo-4H-chromene derivatives containing sulfur-nitrogen heterocycles . Phosphorus Sulfur Silicon , 184 : 2358 – 2392 .
  • 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. and Cai , S. X. 2004 . J. Med. Chem. , 47 : 6299 – 6304 .
  • Dyachenko , V. D. and Chernega , A. N. 2006 . 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 , 42 : 567 – 576 .
  • Ballini , R. , Bosica , G. , Conforti , M. L. , Maggi , R. , Mazzacanni , A. , Righi , P. and Sartori , G. 2001 . Three-component process for the synthesis of 2-amino-2-chromenes in aqueous media . Tetrahedron , 57 : 1395 – 1398 .
  • Rong , L. , Li , X. , Wang , H. , Shi , D. , Tu , S. and Zhuang , Q. 2006 . Efficient green procedure for the Knoevenagel condensation under solvent-free conditions . Synth. Commun. , 36 : 2407 – 2412 .
  • Maggi , R. , Ballini , R. , Sartori , G. and Sartorio , R. 2004 . Basic alumina catalysed synthesis of substituted 2-amino-2-chromenes via three-component reaction . Tetrahedron Lett. , 45 : 2297
  • Heravi , M. M. , Baghernejad , B. and Oskooie , H. A. 2008 . A novel and efficient catalyst to one-pot synthesis of 2-amino-4H-chromenes by methanesulfonic acid . J. Chin. Chem. Soc. , 55 : 3 – 7 .
  • Kidwai , M. , Saxena , S. , Khan , M. K.R. and Thukral , S. S. 2005 . Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents . Bioorg. Med. Chem. Lett. , 15 : 4295 – 4298 .
  • Kumar , A. , Sharma , S. , Maurya , R. A. and Sarkar , J. 2010 . Diversity oriented synthesis of benzoxanthene and benzochromene libraries via one-pot, three-component reactions and their anti-proliferative activity . J. Comb. Chem. , 12 : 20 – 24 .
  • Zhou , D. , Ren , Z. , Cao , W. , Chena , J. and Deng , H. 2008 . Solvent-free one-pot approach for synthesis of substituted 2-aminochromenes . J. Heterocyclic Chem. , 45 : 1865 – 1867 .
  • Mandar , P. , Surpur , S. K. and Shriniwas , D. S. 2009 . 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 , 50 : 719 – 722 .
  • Jin , T. S.H. , Xiao , J. C.H. , Wang , S. J. and Li , T. S.H. 2004 . Ultrasound-assisted synthesis of 2-amino-2-chromenes with cetyltrimethylammonium bromide in aqueous media. . Ultrason. Sonochem , 11 : 393 – 397 .
  • Eshghi , H. and Hassankhani , A. 2005 . Regioselective synthesis of e-oximes catalyzed by ferric chloride under solvent free conditions . Org. Prep. Proced. Int. , 37 : 575 – 582 .
  • Eshghi , H. 2006 . Ferric hydrogensulfate catalysed schmidt reaction of ketones to amides under solvent-free conditions . J Chin. Chem. Soc. , 53 : 987 – 990 .
  • Makarem , S. , Mohammadi , A. A. and Fakhari , A. R. 2008 . A multi-component electro-organic synthesis of 2-amino-4H-chromenes . Tetrahedron Lett. , 49 : 7194 – 7198 .
  • Ahmadjo , S. , Zohuri , G. H. , Damavandi , S. and Sandaroos , R. 2010 . Comparative ethylene polymerization using FI-like zirconium based catalysts . . Reaction Kinet. Mech. Catal. , 101 : 429 – 442 .

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