Preparation of 4-cyano-3-methyl-1-penyl-1H-pyrazole-5-(4-bromophenyl)-nitrile imine: Regio- and stereoselective synthesis of a new class of substituted 3-pyrazolyl-2-pyrazolines and pyrazoles

Heterocycles

Volumn 78, Issue 4, 2009, Pages 911-922

  Mukherjee, Attreyee ^a   Mahalanabis, Kumar K ^a  

^a JADAVPUR UNIVERSITY   (India)

Author keywords

Cycloaddition; Dipolarophile; Fluorescence; Nitrile Imine; Stereoselective

Indexed keywords

EID: 67649397397     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-11531     Document Type: Article

References (58)

1. Sharp J.T. In: Padwa A., and Pearson W.H. (Eds). The Chemistry of Heterocyclic Compounds vol 59 (2002), John Wiley & Sons 473
2. Hassaneen H.M., Mousa H.A.H., Ezmirly S.T., and Shawali A.S. Can. J. Chem. 66 (1988) 1386
3. Wiley R.H., Beur L.C., Fusco R., and Jaboe C.H. Heterocyclic Compounds (1967) 122
4. Dutta Chowdhury S.K., Sarkar M., and Mahalanabis K.K. J. Chem. Res. (2003) 746
5. Mishra M., Dutta Chowdhury S.K., and Mahalanabis K.K. Synth. Commum. 36 (2004) 2681
6. Mahalanabis K.K., Dutta Chowdhury S.K., Sarkar M., and Mishra M. J. Chem. Res. (2006) 78
7. Elguero J. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry II Vol 3 (1996), Pergamon Press, Oxford 1
8. Singh P., Paul K., and Holzer W. Bioorg. Med. Chem. 14 (2006) 5061
9. Azarifar D., and Ghasemnejad H. Molecules 8 (2003) 642
10. Lamberth C. Heterocycles 21 (2007) 1467
11. Singh A., Rathod S., Berad B.N., Patil S.D., and Dosh A.G. Orient. J. Chem. 16 (2000) 315
12. Holla B.S., Akberali P.M., and Shivananda M.K. Farmaco 55 (2000) 256
13. Palaska U.E., Aytemir M., Tayfun I., Erol K., and Dilek E. Eur. J. Med. Chem. Chim. Ther. 36 (2001) 539
14. Goodell J.R., Puig-Basagoiti F., Forshey B.M., Shi P.-Y., and Ferguson D.M. J. Med. Chem. 49 (2006) 2127
15. Kedar R.M., Vidhale N.N., and Chincholkar M.M. Orient. J. Chem. 13 (1997) 143
16. Kucukguzel S.G., and Rollas S. Farmaco 57 (2002) 583
17. Jeong T.-S., Kim K.S., An S.-J., Cho K.-H., Lee S., and Lee W.S. Bioorg. Med. Chem. Lett. 14 (2004) 2715
18. Wang M., Zhang J., Liu J., Xu C., and Ju H. J. Luminescence 99 (2002) 79
19. Jin M., Lu R., Bao C.Y., Xu T.H., and Zhao Y.Y. Optical Materials 26 (2004) 85
20. Oh S.W., Zhang D.R., and Kang Y.S. Material Science Engineering: C 24 (2004) 131
21. Arrieta A., Carrillo J.R., Cossio F.P., Diaz-Ortiz A., Gomez-Escalonilla M.J., de la Hoz A., Langa F., and Moreno A. Tetrahedron 54 (1998) 13167
22. Azarifar D., and Shaebanzadeh M. Molecules 7 (2002) 885
23. Bratenko M.K., A Chornous V., and Vovk M.V. Russ. J. Org. Chem. 37 (2001) 556
24. Hassaneen H.M., Mousa H.A.H., Abed N.M., and Shawali A.S. Heterocycles 27 (1988) 695
25. Tanaka S., and Tarada A. Heterocycles 16 (1981) 717
26. Hassaneen H.M., Shawali A.S., and Elwan N.M. Heterocycles 31 (1990) 1041
27. Diaz-Ortiz A., de la Hoz A., and Langa F. Green Chem. 2 (2000) 165
28. rd Edn (1973), ELBS and Longmann 121
29. Scott F.L., Cronin D.A., and O'Halloran J.K. J. Chem. Soc. (C) (1971) 2769
30. Tobin J.C., Hegarty A.F., and Scott F.L. J. Chem. Soc (B) (1971) 2198
31. Butler R.N., and Scott F.L. J. Chem. Soc. (C) (1968) 1711
32. Joshi K.C., Jain R., and Sharma K. Ind. J. Chem. Sec. B 29 (1990) 895
33. Wolkoff P. Can. J. Chem. 53 (1975) 1333
34. Houk K.N., and Yamaguchi K. In: Padwa A. (Ed). 1,3-Dipolar Cycladdition Chemistry vol 2 (1984), Wiley, New York 407
35. Fliege W., Huisgen R., Clovis J.S., and Knupfer H. Chem. Ber. 116 (1983) 3039
36. Huisgen R., Scidel M., Wallbillich G., and Knupfer H. Tetrahedron 17 (1962) 36
37. Huisgen R., Ooms P.H.J., Mingin M., and Allinger N.L. J. Am. Chem. Soc 102 (1980) 3951
38. Huisgen R., Knupfer H., Sustmann R., Wallbillich G., and Weberndörfer V. Chem. Ber. 100 (1967) 1580
39. Chatterjee S., Banerjee P., Pramanik S., Mukhrjee A., Mahalanabis K.K., and Bhattacharyya S.C. Chem. Phys. Lett. 440 (2007) 313
40. Xiao D., Xi L., Yang W., Fu H., Shuai Z., Fang Y., and Yao J. J. Am. Chem. Soc 125 (2003) 6740
41. Barbera J., Clays K.K., Gimenez R., Houbrechts S., Persoons A., and Serrano J.L. J. Mater. Chem. 8 (1998) 1725
42. Yin J.S., and Wang Z.L. Phys. Rev. Lett. 79 (1997) 2570
43. Fu H.-B., Xie R.-M., Wang Y.-Q., Yao J.-N., and Surf Col.A. Phys. Eng. Asp. 174 (2000) 367
44. Pramanik S., Banerjee P., Sarkar A., Mukherjee A., Mahalanabis K.K., and Bhattacharyya S.C. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (2008) doi: 10.1016/j.saa.2008.04.01
45. Alberti M.J., Auten E.P., Lackey K.E., McDonald O.B., Wood E.R., Preugschat F., Cutler G.J., Kane-Carson L., Liu W., and Jung D.K. Bioorg. Med. Chem. Lett. 15 (2005) 3778
46. Shirai F., Azami H., Kayakiri N., Okumura K., and Nakamura K. PCT Int. Appl. (2004) 436 WO 2004050632
47. Shirai F., Azami H., Kayakiri N., Okumura K., and Nakamura K. Chem. Abstr. 141 (2004) 54327
48. Butler A., and Walker J.V. Chem. Rev. 93 (1993) 1937
49. Zhao D., Fei Z., Geldbach T.J., Scopelliti R., and Dyson P.J. J. Am. Chem. Soc. 126 (2004) 15876
50. Yao Q., Kinney E.P., and Zheng C. Org. Lett. 6 (2004) 2997
51. DeVashre R.B., Moore L.R., and Shaughnessy K.H.J. J. Org. Chem. 69 (2004) 7919
52. Hartwig J.F. Angew. Chem. Int. Ed. 37 (1998) 2046
53. Silinsh E.A. Organic Molecular Crystals: Their Electronic States (1980), Springer-Verlag, Berlin
54. De Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T., Huxley A.J.M., Rademacher J.T., and Rice T.E. Chem. Rev. 97 (1997) 1515
55. Xiao D., Xi L., Yang W., Fu H., Shuai Z., Fang Y., and Yao J. J. Am. Chem. Soc. 125 (2003) 6740
56. Fu H.B., and Yao J.N. J. Am. Chem. Soc. 123 (2001) 1434
57. Oh S.W., and Kang Y.S. Colloids and Surfaces A: Physicochem. Eng. Aspects 415 (2005) 257
58. Fu H.B., Loo B.H., Xiao D.B., Xie R.M., Ji X.H., Yao J.N., Zhag B.W., and Zhang L.Q. Angew. Chem. Int. Ed. 41 (2002) 962