Synthesis of new tripodal Hantzsch 1,4-dihydropyridines under solvent-free condition and their conversion to the corresponding tripodal pyridines

Molecular Diversity

Volumn 14, Issue 4, 2010, Pages 809-813

  Zolfigol, Mohammad Ali ^a   Kolvari, Eskandar ^a   Abdoli, Abbas ^a   Shiri, Morteza ^b  

^a BU ALI SINA UNIVERSITY   (Iran)

^b NONE

Author keywords

1,4 Dihydropyridines; NH4F; Oxone ; Solvent free; Tripodal 1,4 dihydropyridines; Tripodal pyridines

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE; PYRIDINE DERIVATIVE; SODIUM PEROXIDE;

AROMATIZATION; ARTICLE; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

CATALYSIS; CYCLIZATION; DIHYDROPYRIDINES; MODELS, BIOLOGICAL; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; PYRIDINES; SOLVENTS; STEREOISOMERISM;

EID: 78650170135     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-009-9171-7     Document Type: Article

References (27)

1. I Ugi 1997 Multi-component reactions (MCRs). I: prospectives of multi-component reactions and their libraries Adv Synth Catal 339 499 516 1:CAS:528:DyaK2sXltlCjtLY%3D
2. Sharma GVM, Reddy KL, Lakshmi PS, Krishna PR (2006) 'In situ' generated 'HCl'-an efficient catalyst for solvent-free Hantzsch reaction at room temperature: synthesis of new dihydropyridine glycoconjugates. Synthesis 55-58. doi: 10.1055/s-2005-921744 (Pubitemid 43117330)
3. R Miri K Javidnia H Sarkarzadeh B Hemmateenejad 2006 Synthesis, study of 3D structures, and pharmacological activities of lipophilic nitroimidazolyl-1, 4-dihydropyridines as calcium channel antagonist Bioorg Med Chem 14 4842 4849 10.1016/j.bmc.2006.03.016 1:CAS:528:DC%2BD28XltFOmtbs%3D 10.1016/j.bmc.2006.03. 016 16603367
4. A Ghorbani-Choghamarani MA Zolfigol P Salehi E Ghaemi E Madrakian H Nasr-Isfahanid M Shahamirian 2008 An efficient procedure for the synthesis of Hantzsch 1,4-dihydropyridines under mild conditions Acta Chim Slov 55 644 647 1:CAS:528:DC%2BD1cXhsFWmsLzJ
5. ML Kantam T Ramani L Chakrapani BM Choudary 2009 Synthesis of 1,4-dihydropyridine derivatives using nanocrystalline copper(II) oxide catalyst Catal Commun 10 370 372 10.1016/j.catcom.2008.09.023 1:CAS:528: DC%2BD1cXhsVKhtrrJ 10.1016/j.catcom.2008.09.023
6. N Tewari N Dwivedi RP Tripathi 2004 Tetrabutylammonium hydrogen sulfate catalyzed eco-friendly and efficient synthesis of glycosyl 1,4-dihydropyridines Tetrahedron Lett 45 9011 9014 10.1016/j.tetlet.2004.10.057 1:CAS:528: DC%2BD2cXpsVGqt7c%3D 10.1016/j.tetlet.2004.10.057 (Pubitemid 39516928)
7. X Cai H Yang G Zhang 2005 Aromatization of 1,4-dihydropyridines with selenium dioxide Can J Chem 83 273 275 10.1139/v05-058 1:CAS:528: DC%2BD2MXktFeltL8%3D 10.1139/v05-058 (Pubitemid 40768932)
8. M Litvic I Cepanec M Filipan K Kos A Bartolincic V Druskovic MM Tibi V Vinkovic 2005 Mild, selective, and high-yield oxidation of Hantzsch 1,4-dihydropyridines with lead(IV) acetate Hetrocycles 65 23 35 10.3987/COM-04-10194 1:CAS:528:DC%2BD2MXot1ersA%3D%3D 10.3987/COM-04-10194
9. Liu Z, Han B, Liu Q, Zhang W, Yang L, Liu ZL, Yu W (2005) Selective reduction exocyclic double bond of isoxazolones and pyrazolones by Hantzsch 1,4-dihydropyridine. Synlett 1579-1580
10. M Adharvana Chari K Syamasundar 2005 Silica gel/NaHSo4 catalyzed one-pot synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature Catal Commun 6 624 626 10.1016/j.catcom.2005.03.010 1:CAS:528:DC%2BD2MXns1Snt7w%3D 10.1016/j.catcom.2005.03.010 (Pubitemid 41131731)
11. Ji SJ, Jiang ZQ, Lu J, Loh TP (2004) Facile ionic liquids-promoted one-pot synthesis of polyhydroquinoline derivatives under solvent free conditions. Synlett 831-835. doi: 10.1055/s-2004-820035
12. G Sabitha GSKK Reddy CS Reddy JS Yadav 2003 A novel TMSI-mediated synthesis of Hantzsch 1,4-dihydropyridines at ambient temperature Tetrahedron Lett 44 4129 4131 10.1016/S0040-4039(03)00813-X 1:CAS:528:DC%2BD3sXjsVGgsr4%3D 10.1016/S0040-4039(03)00813-X (Pubitemid 36549145)
13. JL Harper CS Camerini-Otero AH Li SA Kim KA Jacobson JW Daly 2003 Dihydropyridines as inhibitors of capacitative calcium entry in Leukemic HL-60 Cells Biochem Pharmacol 65 329 338 10.1016/S0006-2952(02)01488-0 1:CAS:528:DC%2BD3sXivVKjuw%3D%3D 10.1016/S0006-2952(02)01488-0 12527326 (Pubitemid 36084550)
14. A Zarghi H Sadeghi A Fassihi M Faizi A Shafiee 2003 Synthesis and calcium antagonist activity of 1,4-dihydropyridines containing phenylaminoimidazolyl substituents Farmaco 58 1077 1081 10.1016/S0014-827X(03)00159-9 1:CAS:528:DC%2BD3sXot12isb8%3D 10.1016/S0014-827X(03)00159-9 14572858 (Pubitemid 37323926)
15. MA Zolfigol M Kiany-Borazjani MM Sadeghi HR Memarian I Mohammadpoor-Baltork 2000 Oxidation of 1,4-dihydropyridines under mild and heterogeneous conditions Synth Commun 30 2945 2950 10.1080/00397910008087444 1:CAS:528:DC%2BD3cXlt1Sisr8%3D 10.1080/00397910008087444
16. MA Zolfigol MM Sadeghi I Mohammadpoor-Baltork A Ghorbani-Choghamarani A Taqian-Nasab 2001 Oxidation of 1,4-dihydropyridines under mild and heterogeneous conditions Asian J Chem 13 887 890 1:CAS:528:DC%2BD3MXks1Cksrw%3D
17. 2 as a novel heterogeneous system for the oxidation of 1,4-dihydropyridines under mild conditions Green Chem 4 562 564 10.1039/b208328k 1:CAS:528:DC%2BD38Xpt1Ciu78%3D 10.1039/b208328k
18. N Nakamichi Y Kawashita M Hayashi 2002 Oxidative aromatization of 1,3,5-trisubstituted pyrazolines and Hantzsch 1,4-dihydropyridines by Pd/C in acetic acid Org Lett 4 3955 3957 10.1021/ol0268135 1:CAS:528: DC%2BD38XnsVKmtL8%3D 10.1021/ol0268135 12599501
19. MA Zolfigol M Bagherzadeh K Niknam F Shirini I Mohammadpoor-Baltork A Ghorbani-Choghamarani M Baghbanzadeh 2006 Oxidation of 1,4-dihydropyridines under mild and heterogeneous conditions using solid acids J Iran Chem Soc 3 73 80 1:CAS:528:DC%2BD28XivVWhsr4%3D
20. I Loev KM Snader 1965 The Hantzsch reaction. I. Oxidative dealkylation of certain dihydropyridines J Org Chem 30 1914 1916 10.1021/jo01017a048 1:CAS:528:DyaF2MXktFKku7o%3D 10.1021/jo01017a048
21. Zolfigol MA, Safaiee M (2004) Synthesis of 1,4-dihydropyridines under solvent-free conditions. Synlett 827-828. doi: 10.1055/s-2004-820010
22. MA Zolfigol P Salehi M Safaiee 2006 An efficient and eco-friendly procedure for the synthesis of Hantzsch ethyl 1,4-dihydro-2,6-dimethylpyridine- 3,5-dicarboxylates under mild and green conditions Lett Org Chem 3 153 156 10.2174/157017806775224288 1:CAS:528:DC%2BD28Xit1SjtLY%3D 10.2174/ 157017806775224288
23. MA Zolfigol P Salehi A Khorramabadi-Zad M Shayegh 2007 Iodine-catalyzed synthesis of novel Hantzsch N-hydroxyethyl 1,4-dihydropyridines under mild conditions J Mol Catal Chem 261 88 92 10.1016/j.molcata.2006.07.063 1:CAS:528:DC%2BD28XhtlagsrnK 10.1016/j.molcata.2006.07.063 (Pubitemid 44872970)
24. MA Zolfigol P Salehi M Shiri A Sayadi A Abdoli H Keypour M Rezaeivala K Niknam E Kolvari 2008 A simple and efficient route for the synthesis of di and tri(bis(indolyl) methanes) as new triarylmethanes Mol Divers 12 203 207 10.1007/s11030-008-9091-y 1:CAS:528:DC%2BD1cXhtlWhtb%2FM 10.1007/s11030-008- 9091-y 18841491
25. DC Tahmassebi T Sasaki 1994 Synthesis of a new trialdehyde template for molecular imprinting J Org Chem 59 679 681 10.1021/jo00082a034 1:CAS:528:DyaK2cXhs1CisL0%3D 10.1021/jo00082a034
26. Zolfigol MA, Bagherzadeh M, Madrakian E, Ghaemi E, Taqian-Nasab A (2001) One-pot nitration of ohenols under mild and heterogeneous conditions. J Chem Res (S) 140-142 (Pubitemid 32574079)
27. 3 or silica chloride/oxone system Catal Commun 8 256 260 10.1016/j.catcom.2006.04.006 1:CAS:528:DC%2BD28Xht1ykt7nM 10.1016/j.catcom.2006.04.006 (Pubitemid 44828606)