Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 22
439
Views
27
CrossRef citations to date
0
Altmetric
Original Articles

Highly Chemoselective Condensation of β-Naphthol, Aldehyde, and Urea Catalyzed by Thiamine Hydrochloride

, &
Pages 3424-3432 | Received 08 Apr 2010, Published online: 26 Jul 2011

REFERENCES

  • (a) Shanthi , G. ; Perumal , P. T. InCl3-catalyzed efficient one-pot synthesis of 2-pyrrolo-3′-yloxindoles . Tetrahedron Lett. 2009 , 50 , 3959 – 3962 ; (b) Shirakawa , S. ; Kobayashi , S. Carboxylic acid catalyzed three-component aza-friedel-crafts reactions in water for the synthesis of 3-substituted indoles . Org. Lett. 2006 , 8 , 4939 – 4942 ; (c) Zhang , H. ; Zhou , Z. ; Yao , Z. ; Xu , F. ; Shen , Q. Efficient synthesis of pyrimidinone derivatives by ytterbium chloride–catalyzed Biginelli-type reaction under solvent-free conditions . Tetrahedron Lett. 2009 , 50 , 1622 – 1624 ; (d) Bagley , M. C. ; Lubinu , M. C. Microwave-assisted oxidative aromatization of hantzsch 1,4-dihydropyridines using manganese dioxide . Synthesis 2006 , 1283 – 1288 .
  • (a) Lu , J. ; Ma , H. Iron(III)-catalyzed synthesis of dihydropyrimidinones: Improved conditions for the biginelli reaction . Synlett 2000 , 63 – 64 ; (b) Ramalinga , K. ; Vijayalakshmi , P. ; Kaimal , T. N. B. Bismuth(III)-catalyzed synthesis of dihydropyrimidinones: Improved protocol conditions for the Biginelli reaction . Synlett 2001 , 863 – 865 ; (c) Paraskar , A. S. ; Dewker , G. K. ; Sudalai , A. Cu(OTf)2: A reusable catalyst for high-yield synthesis of 3,4-dihydropyrimidin-2(1H)-ones . Tetrahedron Lett. 2003 , 44 , 3305 – 3308 ; (d) Peng , J. ; Deng , Y. Ionic liquids catalyzed Biginelli reaction under solvent-free conditions . Tetrahedron Lett. 2001 , 42 , 5917 – 5919 .
  • (a) Ross , G. F. ; Herdtweck , E. ; Ugi , I. Stereoselective U-4CRs with 1-amino-5-desoxy-5-thio-2,3,4-O-isobutanoyl-β-D-xylopyranose—An effective and selectively removable chiral auxiliary. Tetrahedron 2002, 58, 6127–6133; (b) Keating , T. A. ; Armstrong , R. W. Molecular diversity via a convertible isocyanide in the ugi four-component condensation. J. Am. Chem. Soc. 1995, 117, 7842–7843; (c) Groger , H. ; Hatam , M. ; Martens , J. Synthese totalgeschützter, nichtproteinogener α -Aminosäuren und Oligopeptide aus 2H-1,3-Oxazinen und 2H-1,3-Benzoxazinen via Ugi-Reaktion. Tetrahedron 1995, 51, 7173–7180; (d) Yamada , T. ; Omote , Y. ; Yamanaka , Y. ; Miyazawa , T. ; Kuwata , S. Synthesis of tripeptides containing α,α -diphenylglycine by the modified Ugi reaction. Synthesis 1998, 991–998.
  • (a) Akiyama , T. ; Matsuda , K. ; Fuchibe , K. HCl-Catalyzed stereoselective mannich reaction in H2O-SDS system . Synlett 2005 , 322 – 324 ; (b) Zhao , G. ; Jiang , T. ; Gao , H. ; Han , B. ; Huang , J. ; Sun , D. Mannich reaction using acidic ionic liquids as catalysts and solvents . Green Chem. 2004 , 6 , 75 – 77 ; (c) Chowdari , N. S. ; Ramachary , D. B. ; Barbas , III. C. F. Organocatalysis in ionic liquids: Highly efficient L-proline-catalyzed direct asymmetric mannich reactions involving ketone and aldehyde nucleophiles . Synlett 2003 , 1906 – 1909 ; (d) Akiyama , T. ; Takaya , J. ; Kagoshima , H. Brønsted acid-catalyzed aza diels-alder reaction of danishefsky's diene with aldimine generated in situ from aldehyde and amine in aqueous media . Tetrahedron Lett. 1999 , 40 , 7831 – 7834 .
  • (a) Li , M. ; Guo , W. S. ; Wen , L. R. ; Li , Y. F. ; Yang , H. Z. One-pot synthesis of biginelli and hantzsch products catalyzed by nontoxic ionic liquid (BMImSac) and structural determination of two products . J. Mol. Catal. A: Chem. 2006 , 258 , 133 – 138 ; (b) Wang , L. M. ; Sheng , J. ; Zhang , L. ; Han , J. W. ; Fan , Z. Y. ; Tian , H. ; Qian , C. T. Facile Yb(OTf)3 promoted one-pot synthesis of polyhydroquinoline derivatives through Hantzsch reaction . Tetrahedron 2005 , 61 , 1539 – 1543 ; (c) Chari , M. A. ; Syamasundar , K. Silica gel/NaHSO4 catalyzed one-pot synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature . Catal. Commun. 2005 , 6 , 624 – 626 ; (d) Ko , S. ; Yao , C. F. Ceric Ammonium Nitrate (CAN) catalyzes the one-pot synthesis of polyhydroquinoline via the Hantzsch reaction . Tetrahedron 2006 , 62 , 7293 – 7299 .
  • (a) Anastas , P. ; Williamson , T. Green Chemistry: Frontiers in Benign Chemical Synthesis and Procedure ; Oxford Science Publications : Oxford , UK , 1998 ; (b) De , S. K. ; Gibbs , R. A. Ruthenium(III) chloride-catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2-(1 H )-ones under solvent-free conditions. Synthesis 2005, 1748–1750 .
  • (a) Kantevari , S. ; Vuppalapati , S. V. N. ; Nagarapu , L. Montmorillonite K10–catalyzed efficient synthesis of amidoalkyl naphthols under solvent–free conditions . Catal. Commun. 2007 , 8 , 1857 – 1862 ; (b) Khodaei , M. M. ; Khosropour , A. R. ; Moghanian , H. A Simple and efficient procedure for the synthesis of amidoalkyl naphthols by p-TSA in solution or under solvent-free conditions . Synlett 2006 , 916 – 920 .
  • Lei , M. ; Ma , L. ; Hu , L. Thiamine hydrochloride as a efficient catalyst for the synthesis of amidoalkyl naphthols . Tetrahedron Lett. 2009 , 50 , 6393 – 6397 .
  • Das , B. ; Laxminarayana , K. ; Ravikanth , B. ; Rao , B. R. Iodine-catalyzed preparation of amidoalkyl naphthols in solution and under solvent-free conditions . J. Mol. Catal. A: Chem. 2007 , 261 , 180 – 183 .
  • Dabiri , M. ; Delbari , A. S. ; Bazgir , A. A Novel three-component, one-pot synthesis of 1,2-dihydro-1-arylnaphtho[1,2- e ][1,3]oxazine-3-one derivatives under microwave-assisted and thermal solvent-free conditions . Synlett 2007 , 821 – 823 .
  • Mosslemin , M. H. ; Nateghi , M. R. ; Mohebat , R. A clean synthesis of oxazino[5,6-f]quinolinone and naphtho[1,2-e]oxazinone derivatives . Monatsh Chem 2008 , 139 , 1247 – 1250 .
  • Khosropour , A. R. ; Khodaei , M. M. ; Moghannian , H. A facile, simple, and convenient method for the synthesis of 14-alkyl or aryl-14-H-dibenzo[a,j]xanthenes catalyzed by pTSA in solution and solvent-free conditions . Synlett 2005 , 955 – 958 .
  • Liu , Y. ; Tao , X. ; Lei , L. ; Zhang , Z. Fluoroboric acid adsorbed on silica-gel-catalyzed synthesis of 14-aryl-14H-dibenzo[a,j]xanthene derivatives . Synth. Commun. 2009 , 39 , 580 – 589 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.