Multistep microwave assisted solvent free green chemical synthesis of 2,7-dihydro-3H-pyridazino[3′,4′:4,5]indolo[3,2-c]quinoline-3,13(12H) -dione

Journal of Chemical Research

Volumn , Issue 3, 2006, Pages 192-198

  Dandia, Anshu ^a   Arya, Kapil ^a   Dhaka, Nidhi ^a  

^a UNIVERSITY OF RAJASTHAN   (India)

Author keywords

2,7 dihydro 3H pyridazino 3 ,4 :4,5 indolo 3,2 c quinoline 3, 13(12H) dione

Indexed keywords

EID: 33645922443     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823406776330666     Document Type: Article

References (65)

1. P.J. Brich, C.J. Grossman and A.G. Hayes, Eur. J. Pharmacol., 1988, 154, 85.
2. M. Kessler, M. Baudry and G. Lynch, Brain Res. b, 1989, 377.
3. J.A. Kemp, A.C. Foster, P.D. lesson, T. Priestly, R. Tridgett, L.L. Iversen and G.N. Woodruff, Proc. Nat. Acad. Sci. USA, 1988, 85, 6547.
4. P.D. Leeson and L.L. Iversen, J. Med. Chem., 1994, 37, 4053.
5. L.M. Pullan and R.J. Powel, Neurosci. Lett., 1992, 148, 199.
6. M. Karez-kubicha, B. Horez and W. Danysz, Neuropharmacology, 1999, 38, 109.
7. T.M. Bare, J. Heterocyl. Chem., 1998, 35, 1171.
8. A. Monge, J. Aldana, M.J. Losa, M. Font, E. Castiella, D. Frechilla, E. Cenarruzabeitia, D.I. Martinez and J. Juan, J. Pharm. Sci. 1993, 82, 526.
9. A. Molina, J.J. Vaquero, J.L. Garcia-Navio, J. Alvariz-Builla, B. Depascual-Teresa, F. Gago and M.M. Rodrigo, J. Org. Chem., 1999, 64, 3907.
10. T.M. Bare, R.B. Sparks, J.R. Empfield, T.W. Davenport and J.A. Mckinney, 9511244 A1 (1995); Chem. Abstr., 1995, 123, 313994.
11. O. Westphal, K. Jahn and W. Heffe, Arch. Pharmac., 1961, 37, 294.
12. T.M. Bare and R.B. Sparks, EU Pat. 516297A (1992);
13. Chem. Abstr., 1993, 119, 8821.
14. J.A. Blair and R.J. Gardner, J. Chem. Soc., 1970, 1714.
15. A. Sharaf, P.L. Schiff, A.N. Tackie, C.H. Phoebe and G.H. Martein, J. Heterocycl. Chem., 1996, 33, 239.
16. C. Auclair and C. Paoletti, J. Med. Chem., 1981, 24, 289;
17. (b) C. Auclair, B. Dugue, B. Meunier and C. Paoletti, Biochemistry, 1986, 25, 1240.
18. P. Helissey, S.G. Ranault, J. Ranult and S. Cross, Chem. Pharm. Bull., 1989, 37, 2413.
19. S. Omura, A. Nakagawa, H. Yamada, T. Hata, A. Furusaki and T. Watanabe, Chem. Pharm. Bull., 1973, 21, 931.
20. A. Nakazato, T. Okubo, T. Kumagai, S. Chaki, K. Tomisawa, M. Nagamina, M. Gotoh, K. Kondoh and M. Yoshida, PCT Int. Appl. WO. 99, 28, 298, 10 Jan. (1999); JP. Appl., 332, (1997), 538;
21. Chem. Abstr., 1999, 131, 31932h.
22. (a) P. Helissay, H. Parot-Lopez, J. Ranault and S. Cross, Eur. J. Med. Chem., 1987, 22, 277;
23. (b) P. Helissay, H. Parot-Lope, J. Ranault and S. Cross, Eur. J. Med. Chem., 1987, 22, 366.
24. J.A. Duine and J. Frank, Trends Biochem., 1981, 6, 289.
25. P.M. Fresneda, P. Molina and S. Delgado, Tetrahedron Lett., 1990, 40, 7275.
26. E.M. Beccalki, G. Broggini, A. Marchesini and E. Rossi, Tetrahedron, 2002, 58, 6673.
27. P. Molina, M. Alajarin and A. Vidal, Tetrahedron, 1990, 46, 1063.
28. F. Trecourt, F. Mongin, M. Mallet and G. Queguiner, Synth. Commun., 1995, 25, 4011.
29. T.P. Czoch, F. Pognan, L. Kaczmarek and J. Boratynski, J. Med. Chem., 1994, 37, 353.
30. T.H.M. Jonckers, B.U.W. Maes, G.L.F. Lemiere, G. Pombouts, L. Pieters, A. Haemers and R.A. Dommisse, Synlett, 2003, 615.
31. P. Helissey, H.P. Lopez, J. Ranault and S. Cross, Chem. Pharm. Bull., 1987, 35, 3547.
32. P. Helissey, S.G. Ranault, J. Ranault and S. Cross, Chem. Pharm. Bull., 1989, 37, 675.
33. W.O. Kermach and N.B. Storey, J. Chem. Soc., 1950, 607.
34. M.A. Khan and J.F. Darocha, J. Heterocycl. Chem., 1978, 15, 913.
35. P.E. Cross and E.R.H. Jones, J. Chem. Soc., 1964, 5919.
36. W.F. Hood, E.T. Sun, R.P. Compton and J.B. Monahan, Eur. J. Pharmacol., 1989, 161, 281.
37. (a) A. Loupy, Microwave in Organic Synthesis Wiley - VCH; Weinheim, 2002;
38. (b) B.L. Hayes, Microwaves Synthesis; Chemistry at the Speed of Light; CEM Publishing; Matthews, NC, 2002.
39. (a) S. Caddick, Tetrahedron, 1995, 51, 10403;
40. (b) R.A. Abramovich, Org. Prep. Proced. Int., 1991, 23, 683;
41. (c) A. Loupy, A. Petit, J. Hamelin, F. Texier-Boullet P. Jacquault and D. Methe, Synthesis, 1998, 1213;
42. (d) R.S. Verma, Green Chem., 1999, 1, 43;
43. (e) P. Lidstrom, J. Tierney, B. Wathey and J. Westman, Tetrahedron, 2001, 57, 9225.
44. (a) S.A. Galema, Chem. Soc. Rev., 1997, 26, 233;
45. (b) M. Larhed, C. Moberg and A. Hallberg, Acc. Chem. Res., 2002, 35, 717;
46. (c) A. Lew, P.O. Krutzik and M.E. Hart, J. Comb. Chem., 2002, 4, 95.
47. (a) A. Dandia, K. Arya, M. Sati and S. Gautam, Tetrahedron, 2004, 60 5253;
48. (b) A. Dandia, K. Arya, M. Sati and P. Sarawgi, J. Fluorine Chem., 2004, 5246;
49. (c) A. Dandia, M. Sati, K. Arya, R. Sharma and A. Loupy, Chem. Pharm. Bull., 2003, 50, 1137;
50. (d) A. Dandia, R. Singh, C. Mérienne, G. Morgant and A. Loupy, Sulfur Letters, 2003, 26,201;
51. (e) A. Dandia, M. Sati, K. Arya and A. Loupy, Heterocycles, 2003, 60, 563;
52. (f) A. Dandia, M. Sati and A. Loupy, Green Chemistry, 2002, 4, 599;
53. (g) A. Dandia, M. Upreti, U.C. Pant, U.C. and B. Rani, J. Chem. Res. (S), 1998, 752;
54. J. Chem. Res. (M), 1998, 3348;
55. (h) A. Dandia, M. Saha and H. Taneja, J. Fluorine Chem., 1998, 90, 17.
56. (a) M. Suarez, A. Loupy, E. Salfran, L. Moran and E. Rolando, Heterocycles, 1999, 15, 21;
57. (b) R. Perez, E. Perez, M. Suarez, L. Gonzalez, A. Loupy, M.L. Jimeno and C. Ochoa, Org. Prep. Proced. Int., 1997, 29, 671;
58. (c) M. Suarez, A. Loupy, E. Perez, L. Moran, G. Gerona, A. Morales and M. Autie, Heterocycl. Commun., 1996, 2, 275.
59. (a) F. Csende, Acta Chim. Slov., 2002, 49, 663;
60. (b) E. Ravina and C.F. Masaguer, Current Med. Chem., 2001, 2, 15.
61. K. Arya PhD Thesis University of Rajasthan, Jaipur, 2004.
62. R.A. Abranovitch and A. Bulman, Synlet, 1992, 795.
63. V. Srider, Indian J. Chem., 1996, 35B, 737.
64. T. Libinska, E. Guibe-Jampet, A. Petit and A. Loupy, Synth. Commun., 1999, 29, 549.
65. D. Villemein and F.T. Starzyk, J. Chem. Educ., 1991, 346.