PEG-Mediated Catalyst-Free Synthesis of Hantzsch 1,4-Dihydropyridines and Polyhydroquinoline Derivatives

REFERENCES

• Clark , J. ; Macquarrie , D. M. A. Handbook of Green Chemistry ; Blackwell : Oxford , 2002 .
   Google Scholar
• Tanaka , K. Solvent-Free Organic Synthesis ; Wiley-VCH : New York , 2003 .
   Google Scholar
• Grieco , P. A. Organic Synthesis in Water ; Blackie Academic and Professional : London , 1998.
   Google Scholar
• Green Reaction Media for Organic Synthesis ; Wiley-VCH : New York , 2003 .
   Google Scholar
• Vasudeven , V. N. ; Rajender , S. V. Microwave-accelerated Suzuki cross-coupling reaction in polyethylene glycol (PEG) . Green Chem. 2001 , 3 , 146 .
   Web of Science ®Google Scholar
• Godfraid , T. ; Miller , R. ; Wibo , M. Calcium antagonism and calcium entry blockade . Pharmacol. Rev. 1986 , 38 , 321 .
   PubMed Web of Science ®Google Scholar
• (a) Bossert , F. ; Meyer , H. ; Wehinger , H. 4-aryldihydropyridines, a new class of highly active calcium antagonists . Angew. Chem., Int. Ed. Engl. 1981 , 20 , 762 ; (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 ; (c) Buhler , F. R. ; Kiowski , W. Calcium antagonists in hypertension . J. Hypertens. 1987 , 5 , S3 ; (d) Sawada , Y. ; Kayakiri , H. ; Abe , Y. ; Mizutani , T. ; Inamura , N. ; Asano , M. ; Hatori , C. ; Aramori , I. ; Oku , T. ; Tanak , H. Discovery of the first non-peptide full agonists for the human bradykinin B2 receptor incorporating 4-(2-picolyloxy)quinoline and 1-(2-picolyl)benzimidazole frameworks . J. Med. Chem. 2004 , 47 , 2853 .
   Web of Science ®Google Scholar
• (a) Xia , J. J. ; Wang , G. W. One-pot synthesis and aromatization of 1,4-dihydropyridines in refluxing water . Synthesis 2005 , 2379 ; (b) Heravi , M. M. ; Behbahani , F. K. ; Oskooie , H. A. ; Shoar , R. H. Catalytic aromatization of Hantzsch 1,4-dihydropyridines by ferric perchlorate in acetic acid . Tetrahedron Lett. 2005 , 46 , 2775 ; (c) Bagley , M. C. ; Lubinu , M. C. Microwave-assisted oxidative aromatization of Hantzsch 1,4-dihydropyridines using manganese dioxide . Synthesis 2006 , 1283 ; (d) Adibi , H. ; Hajipour , A. R. A convenient and efficient protocol for oxidative aromatization of Hantzsch 1,4-dihydropyridines using benzyltriphenylphosphonium peroxymonosulfate under almost neutral reaction conditions . Bioorg. Med. Chem. Lett. 2007 , 17 , 1008 .
   Google Scholar
• Itoh , T. ; Nagata , K. ; Miyazaki , M. ; Ishikawa , H. ; Kurihara , A. ; Ohsawa , A. A selective reductive amination of aldehydes by the use of Hantzsch dihydropyridines as reductant . Tetrahedron 2004 , 60 , 6649 .
   Web of Science ®Google Scholar
• Hantzsch , A. Uber die synthese pyridinartiger verbindungen aus acetessigäther und aldehydammoniak . Justus Liebigs Ann. Chem. 1882 , 215 , 1 .
   Google Scholar
• (a) Agarwal , A. ; Chauhan , P. M. S. Solid-supported synthesis of structurally diverse dihydropyrido[2,3-d]pyrimidines using microwave irradiation. Tetrahedron Lett. 2005, 46, 1345; (b) Li , M. ; Guo , W. S. ; Wen , L. R. ; Li , Y. F. ; Yang , H. Z. One-pot synthesis of Biginelli and Hantzsch products catalyzed by non-toxic ionic liquid (BMImSac) and structural determination of two products. J. Mol. Catal. A: Chem. 2006, 258, 133; (c) 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; (d) 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; (e) 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; (f) 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; (g) 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. 2007, 261, 88; (h) 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; (i) 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; (j) Ko , S. ; Yao , C. F. Ceric ammonium nitrate (CAN) catalyzes the one-pot synthesis of polyhydroquinoline via the Hantzsch reaction. Tetrahedron 2006, 62, 7293; (k) Perozo-Rondon , E. ; Calvino-Casilda , V. ; Martin-Aranda , R. M. ; Casal , B. ; Duran-Valle , C. J. ; Rojas-Cervantes , M. L. Catalysis by basic carbons: Preparation of dihydropyridines. Appl. Surf. Sci. 2006, 252, 6080; (l) Tewari , N. ; Dwivedi , N. ; Tripathi , R. P. Tetrabutylammonium hydrogen sulfate–catalyzed eco-friendly and efficient synthesis of glycosyl 1,4-dihydropyridines. Tetrahedron Lett. 2004, 45, 9011; (m) Lee , J. H. Synthesis of Hantsch 1,4-dihydropyridines by fermenting bakers' yeast. Tetrahedron Lett. 2005, 46, 7329; (n) Kumar , A. ; Maurya , R. A. Synthesis of polyhydroquinoline derivatives through unsymmetric Hantzsch reaction using organocatalysts. Tetrahedron 2007, 63, 1946; (o) Evdokimor , N. M. ; Magedov , I. V. ; Kireev , A. S. ; Kornienko , A. One-step, three-component synthesis of pyridines and 1,4-dihydropyridines with manifold medicinal utility. Org. Lett. 2006, 8, 899; (p) Sridhar , R. ; Perumal , P. T. A new protocol to synthesize 1,4-dihydropyridines by using 3,4,5-trifluorobenzeneboronic acid as a catalyst in ionic liquid: Synthesis of novel 4-(3-carboxyl-1H-pyrazol-4-yl)-1,4-dihydropyridines. Tetrahedron 2005, 61, 2465; (q) Debache , A. ; Boulcina , R. ; Belfaitah , A. ; Rhouati , S. ; Carbonib , B. One-pot synthesis of 1,4-dihydropyridines via a phenylboronic acid–catalyzed hantzsch three-component reaction. Synlett 2008, 4, 0509; (r) 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, 61, 924; (s) Bandgar , B. P. ; More , P. E. ; Kamble , V. T. ; Totre , J. V. Synthesis of polyhydroquinoline derivatives under aqueous media. Arkivoc 2008, (15), 1.
   Web of Science ®Google Scholar
• (a) Kamal , A. ; Reddy , D. R. Rajendar Polyethylene glycol (PEG) as an efficient recyclable medium for the synthesis of β-amino sulfides . Tetrahedron Lett. 2006 , 47 , 2261 ; (b) Wang , X. ; Quan , Z. ; Wang , F. ; Wang , M. ; Zhang , Z. ; Li , Z. PEG-SO3H as catalyst for 3,4-dihydropyrimidones via biginelli reaction under microwave and solvent-free conditions . Synth. Commun. 2006 , 36 , 451 .
   Web of Science ®Google Scholar
• (a) Madhava Rao , V. ; Damu , G. L. V. ; Sudhakar , D. ; Siddaiah , V. ; Venkata Rao , C. New efficient synthesis and bioactivity of homoisoflavonoids . Arkivoc 2008 , ( 11 ), 285 ; (b) Das , B. ; Venkateswarlu , K. ; Majhi , A. ; Siddaiah , V. ; Ravinder Reddy , K. A facile nuclear bromination of phenols and anilines using NBS in the presence of ammonium acetate as a catalyst . J. Mol. Catal. A: Chem. 2007 , 267 , 30 ; (c) Siddaiah , V. ; Venkata Rao , C. ; Venkateswarlu , S. ; Subbaraju , G. V. A concise synthesis of polyhydroxydihydrochalcones and homoisoflavonoids . Tetrahedron 2006 , 62 , 841 ; (d) Siddaiah , V. ; Venkata Rao , C. ; Venkateswarlu , S. ; Krishnaraju , A. V. ; Subbaraju , G. V. Synthesis, stereochemical assignments, and biological activities of homoisoflavonoids . Bioorg. Med. Chem. 2006 , 14 , 2545 ; (e) Maheswara , M. ; Siddaiah , V. ; Damu , G. L. V. ; Venkata Rao , C. A solvent-free synthesis of coumarins via Pechmann condensation using heterogeneous catalyst . J. Mol. Catal. A: Chem. 2006 , 255 , 49 .
   Google Scholar