Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 13
568
Views
32
CrossRef citations to date
0
Altmetric
Original Articles

Thiamine Hydrochloride–Catalyzed One-Pot Synthesis of 1,4-Dihydropyridine Derivatives Under Solvent-Free Conditions

, &
Pages 1969-1976 | Received 02 Feb 2010, Published online: 02 May 2011

REFERENCES

  • (a) Stout , D. M. ; Meyers , A. I. Recent advances in the chemistry of dihydropyridines . Chem. Rev. 1982 , 82 , 223 – 243 ; (b) Wei , X. Y. ; Rulledge , A. ; Triggle , D. I. Voltage-dependent binding of 1,4-dihydropyridine Ca2+ channel antagonists and activators in cultured neonatal rat ventricular myocytes . J. Mol. Pharmacol. 1989 , 35 , 541 – 552 ; (c) Bossert , F. ; Meyer , H. ; Wehinger , E. 4-Aryldihydropyridines, a new class of highly active calcium antagonists . Angew. Chem., Int. Ed. Engl. 1981 , 20 , 762 – 769 ; (d) Mannhold , R. ; Jablonka , B. ; Voigdt , W. ; Schoenafinger , K. ; Schravan , K. Calcium- and calmodulin-antagonism of elnadipine derivatives: A comparison of structure–activity relationships . Eur. J. Med. Chem. 1992 , 27 , 229 – 235 ; (e) Janis , R. A. ; Triggle , D. J. New developments in calcium ion channel antagonists . J. Med. Chem. 1983 , 26 , 775 – 785 .
  • (a) Sausins , A. ; Duburs , G. Synthesis of 1,4-dihydropyridines by cyclocondensation reactions . Heterocycles 1988 , 27 , 269 – 289 ; (b) Coburn , R. A. ; Wierzba , M. ; Suto , M. J. ; Solo , A. J. ; Triggle , A. M. ; Triggle , D. J. 1,4-Dihydropyridine antagonist activities at the calcium channel: A quantitative structure–activity relationship approach . J. Med. Chem. 1988 , 31 , 2103 – 2107 ; (c) Bocker , R. H. ; Guenguerich , F. P. Oxidation of 4-aryl- and 4-alkyl-substituted 2,6-dimethyl-3,5-bis(alkoxycarbonyl)-1,4-dihydropyridines by human liver microsomes and immunochemical evidence for the involvement of a form of cytochrome P-450 . J. Med. Chem. 1986 , 29 , 1596 – 1603 .
  • (a) Godfraind , T. ; Miller , R. ; Wibo , M. Calcium antagonism and calcium entry blockade. Pharmacol. Rev. 1986, 38, 321–416; (b) Gordeev , M. F. ; Patel , D. V. ; Gordon , E. M. Approaches to combinatorial synthesis of heterocycles: A solid-phase synthesis of 1,4-dihydropyridines. J. Org. Chem. 1996, 26, 924–928; (c) Shan , R. ; Velaskez , C. ; Knaus , E. E. Syntheses, calcium channel agonist–antagonist modulation activities, and nitric oxide release studies of nitrooxyalkyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(2,1,3-benzoxadiazol-4-yl)pyridine-5-carboxylate racemates, enantiomers, and diastereomers. J. Med. Chem. 2004, 47, 254–261; (d) Miri , R. ; Javidnia , K. ; Sarkarzadeh , H. ; Hemmateenejad , B. Synthesis, study of 3D structures, and pharmacological activities of lipophilic nitroimidazolyl-1,4-dihydropyridines as calcium channel antagonist. Bioorg. Med. Chem. 2006, 14, 4842–4849.
  • Hantzsch , A. Ueber die Synthese pyridinartiger Verbindungen aus Acetessigäther und Aldehydammoniak . Justus Liebigs Ann. Chem. 1882 , 215 , 1 – 82 .
  • (a) Anniyappan , M. ; Muralidharan , D. ; Perumal , P. T. Synthesis of Hantzsch 1,4-dihydropyridines under microwave irradiation . Synth. Commum. 2002 , 32 , 659 – 663 ; (b) Bagley , M. C. ; Lubinu , M. C. Microwave-assisted oxidative aromatization of Hantzsch 1,4-dihydropyridines using manganese dioxide . Synlett 2006 , 1283 – 1288 .
  • 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 .
  • Sabitha , G. ; Reddy , G. S. ; Reddy , C. S. ; Yadav , J. S. A novel TMSI-mediated synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature . Tetrahedron Lett. 2003 , 44 , 4129 – 4131 .
  • (a) 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 ; (b) Donelson , J. L. ; Gibbs , R. A. ; De , S. K. An efficient one-pot synthesis of polyhydroquinoline derivatives through the Hantzsch four-component condensation . J. Mol. Catal. A: Chem. 2006 , 256 , 309 – 311 .
  • (a) Ko , S. ; Sastry , M. N. V. ; Lin , C. ; Yao , C. F. Molecular iodine-catalyzed one-pot synthesis of 4-substituted-1,4-dihydropyridine derivatives via Hantzsch reaction . Tetrahedron Lett. 2005 , 46 , 5771 – 5774 ; (b) Zolfigol , M. A. ; Salehi , P. ; Khorramabadi-Zad , A. ; Shayegh , M. Iodine-catalyzed synthesis of novel Hantzsch N-hydroxyethyl 1,4-dihydropyridines under mild conditions . J. Mol. Catal. A: Chem. 2006 , 261 , 88 – 92 .
  • 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 .
  • Maheswara , M. ; Siddaiah , V. ; Rao , Y. K. ; Tzeng , Y. M. ; Sridhar , C. A simple and efficient one-pot synthesis of 1,4-dihydropyridines using heterogeneous catalyst under solvent-free conditions . J. Mol. Catal. A: Chem. 2006 , 260 , 179 – 180 .
  • 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 .
  • Debache , A. ; Boulcina , R. ; Belfaitah , A. ; Rhouati , S. ; Carboni , B. One-pot synthesis of 1,4-dihydropyridines via a phenylboronic acid catalyzed Hantzsch three-component Reaction . Synlett 2008 , 509 – 511 .
  • Kumar , A. ; Maurya , R. A. Efficient synthesis of Hantzsch esters and polyhydroquinoline Derivatives in aqueous micelles . Synlett 2008 , 883 – 885 .
  • Kumar , A. ; Maurya , R. A. Synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction using organocatalysts . Tetrahedron 2007 , 63 , 1946 – 1952 .
  • (a) Noonan , C. ; Baragwanath , L. ; Connon , S. J. Nucleophilic carbene–catalysed oxidative esterification reactions . Tetrahedron Lett. 2008 , 49 , 4003 – 4006 ; (b) Dünkelmann , P. ; Jung , D. K. ; Nitsche , A. ; Demir , A. S. ; Siegert , P. ; Lingen , B. ; Baumann , M. ; Pohl , M. ; Müller , M. Development of a donor–acceptor concept for enzymatic cross-coupling reactions of aldehydes: The first asymmetric cross-benzoin condensation . J. Am. Chem. Soc. 2002 , 124 , 12084 – 12085 ; (c) Orlandi , S. ; Caporale , M. ; Benaglia , M. ; Annunziata , R. Synthesis of new enantiomerically pure C 1- and C 2-symmetric N-alkyl-benzimidazolium and thiazolium salts . Tetrahedron: Asymmetry 2003 , 14 , 3827 – 3830 .
  • Sheibani , H. ; Seifi , M. ; Bazgir , A. Three-component synthesis of pyrimidine and pyrimidinone derivatives in the presence of high-surface-area MgO, a highly effective heterogeneous base catalyst . Synth. Commum. 2009 , 39 , 1055 – 1064 .

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.