A Convenient Synthesis of Novel 1-[2-(Benzimidazol-2-yl)ethoxy]-2,6-diarylpiperidin-4-ones

Synthetic Communications

Volumn 34, Issue 6, 2004, Pages 1105-1116

  Ramalingan, C ^a   Balasubramanian, S ^a   Kabilan, S ^a  

^a ANNAMALAI UNIVERSITY   (India)

Author keywords

Benzimidazole moiety; Cyanoethylation; Piperidine derivatives; Synthetic compounds

Indexed keywords

1 [2 (BENZIMIDAZOL 2 YL)ETHOXY]PIPERIDIN 4 ONE DERIVATIVE; 1,2 PHENYLENEDIAMINE; ACETONITRILE; ACRYLONITRILE; BENZENE; BENZIMIDAZOLE DERIVATIVE; DIOXANE; PIPERIDONE DERIVATIVE; PYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; HYDROXYLATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MELTING POINT; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILITY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 1842585822     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120028643     Document Type: Article

References (41)

1. (a) Angle, S.R.; Breitenbucher, J.G. Studies in Natural Products Chemistry, Stereoselective Synthesis; Atta-ur-Rahman, Ed.; Elsevier: New York, 1995; Vol. 16, Part J, 453-502;
2. (b) Grishina, G.V.; Gaidarova, E.L.; Zefirov, N.S. Chem. Heterocycl. Compd. 1994, 30, 140;
3. (c) Wang, C.-L.; Wuorola, M.A. Org. Prep. Proced. Int. 1992, 24, 585.
4. (a) Takahata, H.; Ouchi, H.; Ichionose, M.; Nemoto, H. Org. Lett. 2002, 4 (20), 3459;
5. (b) Davis, F.A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169;
6. (c) Honda, T.; Kimura, M. Org. Lett. 2000, 2, 3925;
7. (d) Wilkinson, T.; Stehle, N.W.; Beak, P. Org. Lett. 2000, 2 (2), 155;
8. (e) Ojima, I.; Vidal, E.S. J. Org. Chem. 1998, 63, 7999;
9. (f) Amat, M.; Hidalgo, J.; Llor, N.; Bosch, J. Tetrahedron: Asymmetry 1998, 9, 2419.
10. (a) Ritcher, J.E. Am. J. Gastroenterol. 1997, 92, 34;
11. (b) Al. Muhaimeed, H.J. J. Int. Med. Res. 1997, 25, 175.
12. Evans, D.; Kicks, T.A.; Williamson, W.R.N.; Dawson, N.V.; Meacocok, S.C.R.; Kitchen, E.A. Eur. J. Med. Chem. 1996, 31, 635.
13. Ojha, V.; Singh, J.; Bhakuni, D.S.; Singh, S.; Chatterjee, R.K. Indian J. Chem. 1991, 30B, 324.
14. Asobo, P.F.; Wahe, H.; Mabafor, J.T.; Nkengfack, A.E.; Fomum, Z.T.; Sopbue, E.F.; Döpp, D. J. Chem. Soc., Perkin Trans. 2001, 1, 457.
15. (a) Shetgiri, N.P.; Kokitkar, S.V. Indian J. Chem. 2001, 40B, 163;
16. (b) Habib, N.S.; Soliman, R.; Ashour, F.A.; El. Taiebi, M. Pharmazie 1997, 52, 844;
17. (c) Salluja, S.; Zou, R.; Drach, J.C.; Townsend, L.B. J. Med. Chem. 1996, 39, 881;
18. (d) Townsend, L.B.; Wise, D.S. Parasitol. Today 1990, 6, 106.
19. (a) Göker, H.; Kus, G.; Boykin, D.W.; Yildiz, S.; Altanlar, N. Bioorg. Med. Chem. 2002, 10, 2589;
20. (b) Göker, H.; Tuncbilek, M.; Suzen, S.; Kus, C.; Altanlar, N. Arch. Pharm. Pharm. Med. Chem. 2001, 334, 138.
21. Göker, H.; Kilicigil, G.A.; Tuncbilek, M.; Kus, C.; Ertan, R.; Kendi, E.; Ozbey, S.; Fort, M.; Garcia, C.; Farre, A.J. Heterocycles 1999, 51, 2561.
22. Kumar, D.; Jacob, M.R.; Reynolds, M.B.; Kerwin, S.M. Bioorg. Med. Chem. 2002, 10, 3997.
23. Kubo, K.; Indada, Y.; Kohara, Y.; Sugiures, Y.; Mamiojima; Itoh, K.; Furukawa, Y.; Nighiugaky, K.; Takehiko. J. Med. Chem. 1993, 36 (12), 1772.
24. Rodriguez, M.L.L.; Benhamu, B.; Viso, A.; Morcillo, M.J.; Murcia, M.; Orensanz, L.; Alfaro, M.J.; Martin, M.I. Bioorg. Med. Chem. 1999, 7, 2271.
25. Sharma, S.; Abuzar, S. Prog. Drug. Res. 1983, 27, 85.
26. Garuti, L.; Roberti, M.; Malagoli, M.; Rossi, T.; Castelli, M. Bioorg. Med. Chem. Lett. 2000, 10, 2193.
27. (a) Silverman, R.B. Organic Chemistry of Drug Design and Drug Action; Academic Press Inc: San Diego, 1992;
28. (b) Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555.
29. (a) Balsubramanian, S.; Ramalingan, C.; Kabilan, S. Synth. Commun. 2003, 33 (17), 2979;
30. (b) Ramalingan, C.; Balasubramanian, S.; Kabilan, S. Synth. Commun. 2003, 33 (9), 1443;
31. (c) Balasubramanian, S.; Ramalingan, C.; Kabilan, S. Indian J. Chem. 2002, 41B, 2402;
32. (d) Ramalingan, C.; Balasubramanian, S.; Kabilan, S.; Vasudevan, M. Med. Chem. Res. 2003, 12 (1), 26;
33. (e) Ramalingan, C.; Balasubramanian, S.; Kabilan, S. Heterocycl. Commun. (Communicated).
34. (a) Hudlicky, M. Oxidations in Organic Chemistry; American Chemical Society: Washington, 1990; 186;
35. (b) Krow, G.R. Tetrahedron 1981, 37, 2697.
36. Sughanya, V. Ph.D. Thesis, Annamalai University; 1999.
37. Tokmurzin, KI.Kh.; Kozyren, V.V.; Sharifkanov, A.Sh. Chim. Geterotsikl. Soedin, 1982, 10, 1342.
38. Ramalingan, C. Ph.D. Thesis, Annamalai University; 2002.
39. (a) Bruson, H.A. Organic Reactions; Bachmann, W.E., Fieser, L.F., Blatt, A.H., Johnson, J.R., Eds.; Cyanoethylation, John Wiley & Sons: New York, 1949; Vol. 5, Chap. 2, 79-135;
40. (b) Szabolajos; Gyoergy, K.; Alaios, K.; Pal, K.; Csabc, S. Heterocycles 1995, 40 (1), 155.
41. Noller, C.R.; Baliah, V. J. Am. Chem. Soc. 1948, 70, 3853.