A clean procedure for the synthesis of 1,4-dihydropyridines via Hantzsch reaction in water

References

• Dömling A , Ugi I . Multicomponent reactions with isocyanides . Angew Chem Int Ed . 2000 ; 39 18 : 3168 – 3210 . doi: 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U
   PubMed Web of Science ®Google Scholar
• Zhu , J and Bienayme , H. 2005 . Multi component reactions , Weinheim : Wiley-VCH .
   Google Scholar
• Dömling A. Recent developments in isocyanide based multicomponent reactions in applied chemistry . Chem Rev . 2006 ; 106 1 : 17 – 89 . doi: 10.1021/cr0505728
   PubMed Web of Science ®Google Scholar
• Kalinski C , Lemoine H , Schmidt J , Burdack C , Kolb J , Umkehrer M , Ross G . Multicomponent reactions as a powerful tool for generic drug synthesis Synthesis . 2008 ; 24 : 4007 – 4011 .
   Web of Science ®Google Scholar
• Bocker RH , Guengerich EPJ . 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 – 1601 .
   PubMed Web of Science ®Google Scholar
• Janis RA , Triggle DA . New developments in calcium ion channel antagonists J Med Chem . 1983 ; 25 : 775 – 779 . doi: 10.1021/jm00360a001
   Web of Science ®Google Scholar
• Sirisha K , Bikshapathi D , Achaiah G , Reddy VM . Synthesis, antibacterial and antimycobacterial activities of some new 4-aryl/heteroaryl-2,6-dimethyl-3,5-bis-N-(aryl)-carbamoyl-1,4-dihydropyridines . Eur J Med Chem . 2011 ; 46 5 : 1564 – 1571 . doi: 10.1016/j.ejmech.2011.02.003
   PubMed Web of Science ®Google Scholar
• Lu J , Bai Y-J , Yang B-Q , Ma H-R . Improved synthesis and aromatization of 1,4 - dihydropyridines Chin J Org Chem . 2000 ; 4 : 514 – 517 .
   Google Scholar
• Shi D-Q , Mou J , Zhuang Q-Y , Wang X-S , Tu S-J . One-pot synthesis of 4-aryl-1,4-dihydropyridines in water Chin J Org Chem . 2004 ; 9 : 1042 – 1044 .
   Google Scholar
• Hantzsch A . Ueber die synthese pyridinartiger verbindungen aus acetessigäther und aldehydammoniak Justus Liebigs Ann. Chem . 1882 ; 215 : 1 . doi: 10.1002/jlac.18822150102
   Google Scholar
• Reddy CS , Raghu M . Facile ZrCl4 promoted four-component coupling one-pot synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction Indian J Chem B . 2008 ; 47B : 1578 – 1582 .
   Google Scholar
• Ko S , Sastry MNV , Lin C , Yao CF . Molecular iodinecatalyzed one-pot synthesis of 4-substituted-1,4-dihydropyridine derivatives via Hantzsch reaction Tetrahedron Lett . 2005 ; 46 : 5771 – 5774 . doi: 10.1016/j.tetlet.2005.05.148
   Web of Science ®Google Scholar
• Zolfigol MA , Safaiee M . Synthesis of 1,4-dihydropyridines under solvent-free conditions Synlett . 2004 ; 5 : 827 – 829 . doi: 10.1055/s-2004-820010
   Web of Science ®Google Scholar
• Nandi GC , Samai S , Singh MS . Biginelli and Hantzsch-type reactions leading to highly functionalized dihydropyrimidinone, thiocoumarin, and pyridopyrimidinone frameworks via ring annulation with β-oxodithioesters . J Org Chem . 2010 ; 75 22 : 7785 – 7795 .
   PubMedGoogle Scholar
• Liang J-C , Yeh J-L , Wang C-S , Liou S-F , Tsai C-H , Chen I-J . The new generation dihydropyridine type calcium blockers, bearing 4-phenyl oxypropanolamine, display α-/β-Adrenoceptor antagonist and long-Acting antihypertensive activities . Bioorg Med Chem . 2002 ; 10 3 : 719 – 730 . doi: 10.1016/S0968-0896(01)00318-2
   PubMedGoogle Scholar
• Rafiee E , Eavani S , Rashidzadeh S , Joshaghani M . Silica supported 12-tungstophosphoric acid catalysts for synthesis of 1,4-dihydropyridines under solvent-free conditions . Inorg Chim Acta . 2009 ; 362 : 3555 – 3562 . doi: 10.1016/j.ica.2009.03.049
   Web of Science ®Google Scholar
• Antonyraj CA , Kannan S . Hantzsch pyridine synthesis using hydrotalcites or hydrotalcite-like materials as solid base catalysts Appl Catal A: Gen . 2008 ; 338 : 121 – 129 . doi: 10.1016/j.apcata.2007.12.028
   Web of Science ®Google Scholar
• Shen L , Cao S , Wu J , Li H , Zhang J , Wu M , Qian X . K2CO3-assisted one-pot sequential synthesis of 2-trifluoromethyl-6-difluoromethylpyridine-3,5-dicarboxylates under solvent-free conditions . Tetrahedron Lett . 2010 ; 51 37 : 4866 – 4869 . doi: 10.1016/j.tetlet.2010.07.041
   Google Scholar
• Lee JH . Synthesis of Hantsch 1,4-dihydropyridines by fermenting bakers' yeast . Tetrahedron Lett . 2005 ; 46 43 : 7329 – 7330 . doi: 10.1016/j.tetlet.2005.08.137
   Google Scholar
• Wang J-L , Liu B-K , Yin C , Wu Q , Lin X-F . Candida antarctica lipase B-catalyzed the unprecedented three-component Hantzsch-type reaction of aldehyde with acetamide and 1,3-dicarbonyl compounds in non-aqueous solvent Tetrahedron . 2011 ; 67 14 : 2689 – 2692 . doi: 10.1016/j.tet.2011.01.045
   Google Scholar
• Baghbanian SM , Khaksar S , Vahdat SM , Farhang M , Tajbakhsh M . One-step, synthesis of Hantzsch esters and polyhydroquinoline derivatives using new organocatalyst . Chin Chem Lett . 2010 ; 21 5 : 563 – 567 . doi: 10.1016/j.cclet.2009.12.011
   Web of Science ®Google Scholar
• Pajuste K , Plotniece A , Kore K , Intenberga L , Cekavicus B , Kaldre D . Use of pyridinium ionic liquids as catalysts for the synthesis of 3,5-bis(dodecyloxycarbonyl)-1,4-dihydropyridine derivative Cent Eur J Chem . 2011 ; 9 : 143 – 148 . doi: 10.2478/s11532-010-0132-x
   Google Scholar
• Reddy BP , Rajesh K , Vijayakumar V . Ionic liquid [tbmim]Cl2/AlCl3 under ultrasonic irradiation towards synthesis of 1,4-DHP's Arab J Chem . 2011 . doi: org/10.1016/j.arabjc.2011.01.027
   Google Scholar
• Saha M , Roy S , Chaudhuri SK , Bhar S . Microwave-assisted ammonium formate-mediated synthesis of Hanstzch dihydropyridines under solvent-free conditions – a green protocol Green Chem Lett Rev . 2008 ; 1 : 99 – 102 . doi: 10.1080/17518250802095034
   Web of Science ®Google Scholar
• Goswarmi P . One pot synthesis of unsymmetrical dihydropyridines by green, catalyst free and environmentally benign protocol Green Chem Lett Rev . 2009 ; 1 : 173 – 177 .
   Google Scholar
• Tamaddon F , Razmi Z , Jafari AA . Synthesis of 3,4-dihydropyrimidin-2(1H)-ones and 1,4-dihydropyridines using ammonium carbonate in water . Tetrahedron Lett . 2010 ; 51 8 : 1187 – 1189 . doi: 10.1016/j.tetlet.2009.12.098
   Web of Science ®Google Scholar
• Palmisano G , Tibiletti F , Penoni A , Colombo F , Tollari S , Garella D , Taglipeitra S , Cravotto G . Ultrasound-enhanced one-pot synthesis of 3-(Het)arylmethyl-4-hydroxycoumarins in water . Ultrason Sonochem . 2011 ; 18 2 : 652 – 660 . doi: 10.1016/j.ultsonch.2010.08.009
   PubMedGoogle Scholar
• Safari J , Banitaba SH , Khalili SD . Cellulose sulfuric acid catalyzed multicomponent reaction for efficient synthesis of 1,4-dihydropyridines via unsymmetrical Hantzsch reaction in aqueous media . J Mol Catal A: Chem . 2011 ; 335 1–2 : 46 – 50 .
   Google Scholar
• Kumar A , Sharma , S . A grinding-induced catalyst- and solvent-free synthesis of highly functionalized 1,4-dihydropyridines via a domino multicomponent reaction Green Chem . 2011 ; 13 : 2017 – 2020 .
   Web of Science ®Google Scholar