One-pot, three-component synthesis of 1,4-dihydropyridines in PEG-400

Synthetic Communications

Volumn 41, Issue 21, 2011, Pages 3251-3258

  Wang, Xicun ^a   Gong, Haipeng ^a   Quan, Zhengjun ^a   Li, Lei ^a   Ye, Helin ^a  

^a NORTHWEST NORMAL UNIVERSITY   (China)

Author keywords

1,4 Dihydropyridines; green synthesis; Hantzsch; PEG 400; three component condensation

Indexed keywords

1,4 DIHYDROPYRIDINE; ALDEHYDE; AMMONIUM ACETATE; MACROGOL 400;

ARTICLE; CHEMICAL REACTION; ONE POT SYNTHESIS; POLLUTION; SYNTHESIS;

EID: 79960648371     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.517888     Document Type: Article

References (31)

1. (a) Bossert, F.; Vater, W. 1, 4-Dihydropyridines: A basis for developing new drugs. Med. Res. Rev. 1989, 9, 291-324; (Pubitemid 19189686)
2. (b) Nakayama, H.; Kasoaka, Y. Chemical identification of binding sites for calcium channel antagonists. Heterocycles 1996, 42, 901-909. (Pubitemid 126455457)
3. (a)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. Mol. Pharmacol. 1989, 35, 541-552; (Pubitemid 19114973)
4. (b) Mannhold, R.; Jablonka, B.; Voigdt, W.; Schoenafinger, K.; Schravan, K. Calcium-and calmodulin-antagonism of elnadipine derivatives: Comparative SAR. Eur. J. Med. Chem. 1992, 27, 229-235.
5. (a) Bretzel, R. G.; Bollen, C. C.; Maeser, E.; Federlin, K. F. Nephroprotective effects of nitrendipine in hypertensive type I and type II diabetic patients. Am. J. Kidney. Dis. 1993, 21, 53-64; (Pubitemid 23180378)
6. (b) Boer, R.; Gekeler, V. Chemosensitizers in tumor therapy: New compounds promise better efficacy. Drugs Future 1995, 20, 499-509.
7. Sabitha, G.; Reddy, G. S. K. K.; 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. (Pubitemid 36549145)
8. 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. (Pubitemid 41131731)
9. 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. (Pubitemid 44755282)
10. 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. (Pubitemid 44247866)
11. 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. (Pubitemid 41019186)
12. (a) Xu, L. W.; Xia, C. G.; Li, J. W.; Zhou, S. L. Efficient Lewis base-catalyzed conjugate addition of azide ion to cyclic enones in water. Synlett 2003, 14, 2246-2248;
13. (b) Yan, Z. Y.; Niu, Y. N.; Wei, H. L.; Wu, L. Y.; Zhao, Y. B.; Liang, Y. M. Combining proline and "click chemistry": A class of versatile organocatalysts for the highly diastereo-and enantioselective Michael addition in water. Tetrahedron: Asymmetry 2006, 17, 3288-3293.
14. (a) Chandrasekhar, S.; Narsihmulu, C.; Saritha, B.; Sultana, S. S. Poly(ethyleneglycol) (PEG): A rapid and recyclable reaction medium for the DABCO-catalyzed Baylis-Hillman reaction. Tetrahedron Lett. 2004, 45, 5865-5867. (Pubitemid 38968569)
15. (b) Chandrasekhar, S.; Reddy, N. R.; Sultana, S. S.; Narsihmulu, C.; Reddy, K. V. L-Proline-catalysed asymmetric aldol reactions in PEG-400 as recyclable medium and transfer aldol reactions. Tetrahedron 2006, 62, 338-345; (Pubitemid 41783865)
16. (c) Habib, F.; Nasser, I.; Mohammad, A. A one-pot, efficient, and odorless synthesis of symmetrical disulfides using organic halides and thiourea in the presence of manganese dioxide and wet polyethylene glycol (PEG-200). Tetrahedron Lett. 2010, 51, 508-509;
17. (d) Habib, F.; Nasser, I.; Mohammad, A. A facile generation of C-S bonds via one-pot, odorless, and efficient thia-Michael addition reactions using alkyl, aryl or allyl halides, thiourea, and electron-deficient alkenes in wet polyethylene glycol (PEG 200) under mild reaction conditions. Tetrahedron 2009, 65, 5293-5301;
18. (e) Zhou, W.-J.; Wang, K.-H.; Wang, J.-X. Pd(PPh3)4-PEG 400-catalyzed protocol for the atom-efficient Stille cross-coupling reaction of organotin with aryl bromides. J. Org. Chem. 2009, 74, 5599-5602;
19. (f) Ackermann, L.; Vicente, R. Catalytic direct arylations in polyethylene glycol (PEG): Recyclable palladium(0) catalyst for CH bond cleavages in the presence of air. Org. Lett. 2009, 11, 4922-4925.
20. (a) Wang, X. C.; Quan, Z. J.; Wang, F.; Wang, M. G.; Zhang, Z.; Li, Z. PEG-SO3H as catalyst for 3,4-dihydropyrimidones via Biginelli reaction under microwave and solventfree conditions. Synth. Commun. 2006, 36, 451-456; (Pubitemid 43175901)
21. (b) Wang, X. C.; Quan, Z. J.; Zhang, Z. Michael additions of dihydropyrimidines and 2-amino-1,3,4-thiadiazoles to a,bethylenic compounds: Using polyethylene glycols as a green reaction media. Tetrahedron 2007, 63, 8227-8233. (Pubitemid 47031240)
22. Love, B.; Snader, K. M. The Hantzsch reaction, I: Oxidative dealkylation of certain dihydropyridines. J. Org. Chem. 1965, 30, 1914-1916.
23. Hinkel, L. E.; Madel, W. R. Substituted aromatic aldehydes in Hantzsch's pyridine condensation, part I: Methoxy-, chloro-, and hydroxy-benzaldehydes. J. Chem. Soc. 1929, 750-754.
24. Watanabe, Y.; Shiota, K.; Hoshiko, T.; Ozaki, S. An efficient procedure for the Hantzsch dihydropyridine synthesis. Synthesis 1983, 9, 761.
25. Phillips, A. P. Hantzsch's pyridine synthesis. J. Am. Chem. Soc. 1949, 71, 4003-4007.
26. Berson, J. A.; Brown, E. Studies on dihydropyridines, II: The photochemical disproportionation of 4-(20-nitrophenyl)-1,4-dihydropyridines. J. Am. Chem. Soc. 1955, 77, 444-447.
27. Loev, B.; Goodman, M. M.; Snader, K. M.; Tedeschi, R.; Macko, E. "Hantzsch-type" dihydropyridine hypotensive agents. J. Med. Chem. 1974, 17, 956-965.
28. Shaabani, A.; Rezayan, A. H.; Rahmati, A.; Sharifi, M. Ultrasound-accelerated synthesis of 1,4-dihydropyridines in an ionic liquid. Monatsh. Chem. 2006, 137, 77-81. (Pubitemid 43016873)
29. Norcross, B. E.; Klinedinst, P. E.; Westheimer, F. H. The reduction of olefinic double bonds with dihydropyridines. J. Am. Chem. Soc. 1962, 84, 797-802.
30. Memarian, H. R.; Sadeghi, M. M.; Momeni, A. R.; Doepp, D. Synthesis and photochemistry of novel 3,5-diacetyl-1,4-dihydropyridines. Monatsh. Chem. 2002, 133, 661-667.
31. Stork, G.; Ohashi, M.; Kamachi, H.; Kakisawa, H. A new pyridine synthesis via 4-(3-oxoalkyl) isoxazoles. J. Org. Chem. 1971, 36, 2784-2786.