Regioselective synthesis of 4′-amino-1′H-spiro[cyclohexane-1, 2′-(pyrimido [1,2-a]benzimidazole)]-3′-carbonitrile in aqueous medium

Journal of Chemical Research

Volumn , Issue 3, 2007, Pages 155-159

  Dandia, Anshu ^a   Sarawgi, Pritima ^a   Bingham, Ann L ^b   Drake, John E ^c   Hursthouse, Michael B ^b   Light, Mark E ^b   Ratnani, Raju ^d  

^a UNIVERSITY OF RAJASTHAN   (India)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^c UNIVERSITY OF WINDSOR   (Canada)

^d M D S UNIVERSITY   (India)

Author keywords

Aqueous media; Benzimidazoles; Fused pyrimidines; Microwave irradiation

Indexed keywords

EID: 34249311290     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823407X198582     Document Type: Article

References (57)

1. (a) C. Ramalingan, S. Balasubramanian and S. Kabilan, Synth. Commun., 2004, 34, 1105;
2. (b) J.E. Ritcher, Am. J. Gastroenterol., 1997, 92, 34;
3. (c) H.J.J. Al Muhaimeed, Int. Med Res., 1997, 25, 175.
4. J.E. De Araujo, J.P. Huston and M. Brandao, Eur. J. Pharm., 2001, 432, 43.
5. S. Khan, R. Whelpton and A.T. Micheal-Titus, Neumsci. Lett., 1996, 205, 33.
6. S. Khan, N. Brooks, R. Whelpton and A.T. Micheal-Titus, Eur. J. Pharm., 1995, 282, 229.
7. N. Wonda and Z. Michal, Arch. Pharm., 1999, 337, 249.
8. G. Trapani, M. Farnco, A. Latrofa, G. Genchi and V. lacobazzi, Eur. J. Med. Chem., 1997, 32, 83.
9. S. Lazarono, A. Popham, and N.J.M. Birdsall, Mol. Pharm., 2002, 62, 1492.
10. A.N. Frolov, Russian J. Gen. Chem., 2001, 71, 553.
11. A. Kreutzbeger and M. Leger, Arzneimittelforschung, 1983, 33, 1517.
12. W. Nawrocka, M. Zimeski, T. Kuznicks and M.W. Kowalska, Arch. Pharm., 1999, 332, 85.
13. A.L. Krasovsky, A.S. Hartulyari, V.G. Nenajdenko and E.S. Balenkova, Synthesis, 2002, 133.
14. W. Nawrocka, B. Sztuba, H. Uszkiewicz, M.W. Kowalska, J. Wietrzyk, D. Nevozhai, and A. Opolski, Polish J. Chem., 2005, 79, 709.
15. V.V. Lipson, V.D. Orlov, S.M. Desenko, S.V. Shishkina, O.V. Shishkin and M.G. Shirobokova, Chem. Heterocycl. Compd, 2000, 36, 1039.
16. H.Y. Afeefy, Boll. Chim. Farm., 1998, 137, 480.
17. P.F. Asobo, H. Wahe, J.T. Mabafor, A.E. Nkengfack, Z.T. Fonum, E.F. Sopbue, and D. Döpp, J. Chem. Soc. Perkin Trans. I, 2001, 457.
18. H. Wahe, P.F. Asobo, R.A. Cherkasov, Z.T. Fomum and D. Döpp, A.E. Nkengfack and G.N. Folefoc, Arkivoc, 2003, xiv, 170.
19. H Wahe, P.F. Asobo, R.A. Cherkasov, Z.T. Fomum and D. Döpp, Arkivoc, 2004, i, 130.
20. K.M. Dawood, A.M. Farag and Z.E. Kandeel, J. Chem. Res. (S), 1999, 88.
21. V.A. Anisinova, M.M. Osipova, A.A. Spasov, A.F. Turchaeva, G.P. Dudchenko, N.P. Larionov and S.G. Kovalev, Pharm. Chem. J., 2002, 36, 468.
22. C. Romano, E. De La Cuesta and C. Avendaño, Heterocycles, 1990, 31, 267.
23. I. Al-Afaleq Eljazi, Synth. Commun., 2000, 30, 1985.
24. (a) T.J. Connolly, P. McGarry and S. Sukhtankar, Green Chem., 2005, 7, 586;
25. (b) R. Liu, C. Dong, X. Liang and X. Hu, J. Org. Chem., 2005, 70, 729;
26. (c) G. Stavber, M. Zupan, M. Jereb and S. Stavber, Org. Lett., 2004, 6, 4973.
27. (a) A. Foucaud, G. Bram and A. Loupy, in Preparative chemistry using supported reagents, P. Laszlo, Ed., Academic Press, New York, 1987, 17, 317;
28. (b) J.H. Clark, Catalysis of organic reactions by supported inorganic reagents, VCH, Weinheim, 1994;
29. (c) G.W. Kabalka and R.M. Pagni, Tetrahedron, 1997, 53, 7999.
30. (a) T. Matsushita, H. Hinou, M. Kurogochi, H. Shimizu and S.-I. Nishimura, Org. Lett. 2005, 7, 877;
31. (b) J.K. Murray and S.H. Gellman, Org. Lett. 2005, 7, 1517;
32. (c) J.K. Murray J. Am. Chem. Soc., 2005, 127, 13271;
33. (d) R.S. Varma, Green Chem. 1999, 43. 25
34. (a) I. Ugi, A. Dömling and W. Hörl, Endeavour, 1994, 18, 115;
35. (b) R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown and T.A. Keating, Acc. Chem. Res., 1996, 29, 123.
36. M. Plunket and J.A. Ellman, Scientific American, 1997, 276, 68;
37. (b) S.L. Schreiber, Discovery Sci., 2000, 287, 1964.
38. S.L. Dax, J.J. McNally and M.A. Youngman, Curr. Med. Chem., 1999, 6, 255.
39. (a) R.S. Varma and D. Kumar, Tetrahedron Lett., 1999, 40, 7665;
40. (b) C. Kappe, D. Kumar and R.S. Varma, Synthesis, 1999, 1799.
41. (a) A. Dandia, P. Sarawgi, M.B. Hursthouse, A.L. Bingham, M.E. Light, J.E. Drake and R. Ratnani, J. Chem. Res., 2006, 445;
42. (b)A. Dandia, R.Singh and S.Khaturia, Bioorg. Med. Chem., 2006, 14, 1303;
43. (c) A. Dandia, K. Arya, M. Sati and S. Gautam, Tetrahedron, 2004, 60, 5253;
44. (d) A. Dandia, M. Sati, K. Arya and A. Loupy, Green Chem., 2002, 4, 599;
45. (e) A. Dandia, H. Sachdeva and R. Singh, J. Chem. Res. (S), 2000, 272,
46. (a) A. Dandia, K. Arya and P. Sarawgi, J. Indian Chem. Soc., 2003, 80, 1183;
47. (b) A. Dandia, K. Arya, M. Sati, and P. Sarawgi, J. Fluorine Chem., 2004, 125, 1273;
48. (c) A. Dandia, K. Arya and M. Sati, Synth. Commun., 2004, 34, 1141.
49. C. Romano, E. De La Cuesta, C. Avendaño, F. Florencio and J. Sainz-Aparicio, Tetrahedron, 1988, 44, 7185.
50. C.G. Chidester and D.J. Anderson, Acta Cryst., 1986, C42, 1769.
51. J.L. Young and W.R. Scheidt, Acta Cryst., 1986, C42, 1652.
52. A. Quick and D.L. Williams, Can. J. Chem., 1979, 54, 2482.
53. A.J.M. Duisenberg, J. Appl. Cryst., 1992, 25, 92.
54. G.M. Sheldrick, SADABS V2., 2003, 10.
55. G.M. Sheldrick, Acta Cryst., 1990, A46, 467.
56. L. J. Farrugia, J. Appl. Cryst., 1999, 32, 837.
57. G.M. Sheldrick, SHELXL97, Structure Determination Software; University of Gottingen, Germany, 1997.