Hantzsch synthesis of 2,6-dimethyl-3,5-dimethoxycarbonyl-4-(o- methoxyphenyl)-1,4-dihydropyridine; a novel cyclisation leading to an unusual formation of 1-amino-2-methoxycarbonyl-3,5-bis(o-methoxyphenyl)-4-oxa- cyclohexan-1-ene

Molecules

Volumn 12, Issue 11, 2007, Pages 2546-2558

  Filipan Litvić, Mirela ^a   Litvić, Mladen ^a   Cepanec, Ivica ^a   Vinković, Vladimir ^b  

^a BELUPO Pharmaceuticals   (Croatia)

^b RUDER BO KOVI INSTITUTE   (Croatia)

Author keywords

Deprotonation; Hantzsch condensation; Intramolecular Michael addition; Substituted pyrane

Indexed keywords

1,4 DIHYDROPYRIDINE; 1,4-DIHYDROPYRIDINE; CYCLOHEXANE DERIVATIVE; DIHYDROPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CRYSTALLIZATION; CYCLIZATION; SYNTHESIS;

CRYSTALLIZATION; CYCLIZATION; CYCLOHEXANES; DIHYDROPYRIDINES; MOLECULAR STRUCTURE;

EID: 36849088594     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12112546     Document Type: Article

References (35)

1. Hantzsch, A. Condensationprodukte aus Aldehydammoniak und ketoniartigen Verbindungen. Chem. Ber. 1881, 14, 1637-1638.
2. a) Eisner, U.; Kuthan, J. The Chemistry of Dihydropyridines. Chem. Rev., 1972, 72, 1-42;
3. b) Stout, D. M.; Meyers, A. I. Recent Advances in the Chemisty of Dihydropyridines. Chem. Rev. 1982, 82, 223-243;
4. c) Sausinš, A.; Duburs, G. Synthesis of 1,4-Dihydropyridines by Cyclocondensation Reactions. Heterocycles, 1988, 27, 269-289;
5. d) Kuthan, J.; Kurfürst, A. Development in Dihydropyridine Chemistry. Ind. Eng. Chem. Prod. Res. Dev. 1982, 21, 191-261;
6. e) Zolfigol, M. A.; Salehi, P.; Safaiee, M. 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. 2006, 3, 153-156;
7. f) Zolfigol, M. A.; Salehi, P.; Khorramabadi-Zad, A.; Shayegh, M. Iodine-catalysed synthesis of novel Hantzsch N-hydroxyethyl 1,4-dihydropyridines under mild conditions. J. Mol. Catal. A: Chem. 2007, 261, 88-92;
8. g) Zolfigol, M. A.; Safaiee, M. Synthesis of 1,4-Dihydropyridines under Solvent-free Conditions. Synthesis, 2004, 827-828.
9. th edition; Merck Research Laboratories: Rahway, NJ, 1996; p. 1121.
10. Boström, S. L.; Ljung, B.; Mårdh, S.; Forsen, S.; Thulin, E. Interaction of the antihypertensive drug felodipine with calmodulin. Nature 1981, 292, 777-778.
11. Iwanami, M.; Shibanuma, T.; Fujimoto, M.; Kawai, R.; Tamazawa, K.; Takenaka, T.; Takahashi, K.; Murakami, M. Synthesis of New Water-soluble Dihydropyridine Vasodilatators. Chem. Pharm. Bull. 1979, 27 1426-1440.
12. Arrowsmith, J. E.; Campbell, S. F.; Cross, P. E.; Stubbs, J. K.; Burges, R. A.; Gardiner, D. G.; Blackburn, K. J. Long-Acting Dihydropyridine Calcium Antagonists. 1. 2-Alkoxymethyl Derivatives Incorporating Basic Substituents. J. Med. Chem. 1986, 29,1696-1702.
13. Berkels, B.; Roesen, R.; Dhein, S.; Fricke, U.; Klaus, W. Dihydropyridine Calcium Antagonist-Induced Modulation of Endothelial Function: A Reviw. Cardiovasc. Drug Rev. 1999, 17, 179-186.
14. Tsuruo, T.; Iida, H.; Nojiri, M.; Tsukagoshi, S.; Sakurai, Y. Circumvention of Vincristine and Adriamycin Resistance in Vitro and in Vivo by Calcium Influx Blockers. Cancer Res. 1983, 43, 2905-2910.
15. Chapman, R. W.; Danko, G.; Siegels, M. I. Effect of Extra- and Intracellular Calcium Blockers on Histamine and Antigen-Induced Bronchospasm in Guinea Pigs and Rats. Pharmacology 1984, 29, 282-291.
16. Malaise, W. J.; Mathias, P. C. F. Stimulation of Insulin Release by Organic Calcium-Agonist. Diabetologia 1985, 28, 153-156.
17. Krauze, A.; Germane, S.; Eberlins, O.; Sturms, I.; Klusa, V.; Duburs, G. Derivatives of 3-cyano-6-phenyl-4-(3′-pyridyl)pyridine-2(1H)-thione and their neurotropic activity. Eur. J. Med. Chem. 1999, 34, 301-310.
18. Peri, R.; Padmanabhan, S.; Singh, S.; Rutledge, A.; Triggle, D. J. Permanently Charged Chiral 1,4-Dihydropyridines: Molecular Probes of L-Type Calcium Channels. Synthesis and Pharmacological Characterization of Methyl (ω-Trimethylalkylammonium) 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5- pyridinedicarboxylate Iodide, Calcium Channel Antagonists J. Med. Chem. 2000, 43, 2906-2914.
19. Zhou, X.; Zhang, L.; Tseng, E.; Scott-Ramsay, E.; Schentag, J. J.; Coburn, R. A.; Morris, M. E. New 4-aryl-1,4-dihydropyridines and 4-arylpyridines as P-glycoprotein inhibitors. Drug. Metab. Dispos. 2005, 33, 321-328.
20. Loev, B.; Goodman, M. M.; Snader, K. M.; Tedeschi, R.; Macko, E. "Hantzsch-Type" Dihydropyridine Hypotensive Agents. J. Med. Chem. 1974, 17, 956-965.
21. Meyer, H.; Bossert, F.; Horstmann, H. Dihydropyridine, II. Synthese Von 1,4-Dihydropyridinen mit Brückenkopf-N-atom. Liebigs Ann. Chem. 1977, 1888-1894.
22. Phillips, A. P. Hantzsch's Pyridine Synthesis. J. Am. Chem. Soc. 1949, 71, 4003-4007.
23. Meyer, H.; Bossert, F.; Wehinger, E.; Stoepel, K.; Vater, W. Synthese und vergleichende pharmakologische Untersuchungen von 1,4-Dihydro-2,6-dimethyl-4- (3-nitrophenyl)pyridin-3,5-dicarbonsäuereestern mit nicht-identischen Esterfunktionen. Arzneim. Forsch. (Drug Res.) 1981, 31, 407-409.
24. 1a Adrenoreceptor-Selective Antagonist That Inhibits Phenylephrine-Induced Contraction of the Human Prostate. J. Med. Chem. 1998, 41, 2643-2650.
25. 1a Adrenoreceptor-Selective Antagonist for the Treatment of Benign Prostatic Hyperplasia. J. Med. Chem. 1998, 41, 5320-5333.
26. Khadilkar, B. M.; Jaisinghani, H. G.; Saraf, M. N.; Desai, S. K. Synthesis and pharmacological studies of new derivatives of dimethyl-1,4- dihydro-2,6-dimethyl-3,5-pyridine dicarboxylate. Ind. J. Chem. 2001, 40B, 82-86.
27. Wang, G.-W.; Miao, C.-B. Environmentally benign one-pot multi-component approaches to the synthesis of novel unsymmetrical 4-arylacridiones. Green Chem. 2006, 8, 1080-1095.
28. Angeles, E.; Santillán, H.; Martínez, I.; Ramírez, A.; Velásquez, A.; López-Castañares, R.; Martínez, R. Rearrangement of o-Nitrobenzaldehyde in the Hantzsch Reaction. Molecules 2001, 6, 683-693.
29. Görlitzer, K.; Fabian, J.; Trittmacher, J. Dimere aus o-Nitrobenzylidenacetessigestern. Pharmazie 2005, 60, 571-573.
30. Litvić, M.; Cepanec, I.; Filipan, M.; Kos, K.; Bartolinčić, A.; Drušković, V.; Tibi, M. M.; Vinković, V. Mild, Selective and High-Yield Oxidation of Hantzsch 1,4-Dihydropyridines with Lead(IV) Acetate. Heterocycles 2005, 65, 23-36.
31. Litvić, M.; Cepanec, I.; Vinković; V. A convenient Hantzsch synthesis of 1,4-dihydropyridines using tetraethyl orthosilicate. Heterocycl. Commun. 2003, 9, 385-390.
32. Litvić, M.; Filipan, M.; Pogorelić, I.; Cepanec, I. Ammonium carbamate; mild, selective and efficient ammonia source for the preparation of β-amino-α,β-unsaturated esters at room temperature. Green Chem. 2005, 7, 771-774.
33. Kim, S. C.; Choi, K. M.; Cheong, C. S. Synthesis of Amlodipine Using Aza Diels-Alder Reaction. Bull. Kor. Chem. Soc. 2002, 23, 143-144.
34. 13C Spectroscopy. Tetrahedron 1986, 42, 5729-5738.
35. Treibs, W.; Beger, J. 4-Aryl-3-carboxy-pyridine als ausgangssubstanzen für N-methyl-1,2-benzisoazalene. Liebigs Ann. Chem. 1962, 652, 192-203.