Studies on pyrimidine-annelated heterocycles: Synthesis of novel pyrazolo[3′,4′:4,5]pyrido[2,3-d]pyrimidines by intramolecular 1,3-dipolar cycloadditions

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 16, 1996, Pages 1999-2003

  Baruah, Bipul ^a   Prajapati, Dipak ^a   Sandhu, Jagir S ^a   Ghosh, Anil C ^a  

^a REGIONAL RESEARCH LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748915610     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960001999     Document Type: Article

References (57)

1. (a) E. Lunt, Comprehensive Organic Chemistry, ed. D. Barton and W. D. Ollis, Pergamon Press, Oxford, 1974, vol. 4, 493;
2. (b) J. D. Brown, Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky and C. W. Rees, Pergamon Press, Oxford, 1984, vol. 3, p. 57;
3. (c) T. Sasaki, K. Minamoto, T. Suzuki and S. Yamashita, Tetrahedron, 1980, 36, 865 and references cited therein;
4. (d) T. K. Bradshaw and D. W. Hutchison, Chem. Soc. Rev., 1977, 6, 43.
5. (a) R. Marumoto and Y. Furukawa, Chem. Pharm. Bull., 1977, 25, 2974;
6. (b) C. C. Cheng and B. Roth, Progr. Med. Chem., 1971, 8, 61;
7. (c) A. S. Jones, J. R. Swgers, R. T. Walker and E. D. Clercq, J. Med. Chem., 1988, 31, 268;
8. (d) H. Griengl, E. Wanck, W. Schwarz, W. Streicher, B. Rosenwirth and E. D. Clercq, J. Med. Chem., 1987, 30, 1199;
9. (e) E. D. Clercq and R. Bernaerts, J. Biol. Chem., 1987, 262, 14905.
10. Certainly functionalisation of uracils at the C-5 and C-6 positions leads to biologically interesting molecules but is not a simple task requiring, rather, sophisticated and tedious reaction conditions see: (a) N. G. Kundu and P. Das, J. Chem. Soc., Chem. Commun., 1995, 99;
11. (b) H. Wamhoff and S. Winfried, J. Org. Chem., 1986, 51, 2787;
12. (c) M. Botta, R. Saladino, D. Lamba and R. Nicolletti, Tetrahedron, 1993, 49, 6053.
13. Recently it has been found that 6-substituted uracils are active against HIV and other viruses see: (a) T. Miyasaka, H. Tanaka, M. Baba, H. Hayakawa, R. T. Walker, J. Balzarini and E. D. Clercq, J. Med. Chem., 1989, 32, 2507;
14. (b) M. Baba, R. Pauwels, P. Herdwig, E. D. Clercq, J. Desmyster and M. Vandepulfe, Biochem. Biophys. Res. Commun., 1987, 142, 128;
15. (b) E. D. Clercq, J. Med. Chem., 1986, 29, 1561;
16. (c) E. D. Clercq, Anticancer Res., 1986, 6, 549.
17. For review see: (a) R. Huisgen, XXIIIrd International Congress of Pure and Applied Chemistry, 1971, 1, 175;
18. (b) R. Huisgen, Angew. Chem., Int. Ed. Engl., 1977, 16, 572;
19. (c) R. Huisgen, Angew. Chem., Int. Ed. Engl., 1980, 19, 947;
20. (d) R. Huisgen, Pure Appl. Chem., 1980, 52, 2283;
21. (e) R. Huisgen, Pure Appl. Chem., 1981, 53, 171;
22. (f) R. Huisgen, C. Fulka, I. Kalwinsch, L. Xingya, G. Mloston, J. R. Moran and A. Probsti, Bull. Soc. Chim. Belg., 1984, 93, 511.
23. (a) Y. Kitahara, T. Kato, M. Funamizu, N. Otatani and H. Izuumi, J. Chem. Soc., Chem. Commun., 1968, 1632;
24. (b) W. M. Grootaert and P. J. De Clercq, Tetrahedron Lett., 1982, 3291 and references cited therein;
25. (c) C. J. Wang, W. C. Ripka and P. N. Confalone, Tetrahedron Lett., 1984, 25, 4613.
26. B. R. Baker, Design of Active Site Directed Irreversible Enzyme Inhibitors, Wiley, New York, 1967;
27. (b) R. K. Robins, Heterocyclic Compounds, ed. R. C. Elderfield, New York, 1967, vol. 8
28. (a) M. Gogoi, P. J. Bhuyan, J. S. Sandhu and J. N. Baruah, J. Chem. Soc., Chem. Commun., 1984, 1549;
29. (b) D. Prajapati, A. Sivaprasad, J. S. Sandhu and J. N. Baruah, Heterocycles, 1984, 22, 1005 and references cited therein;
30. (c) A. Sivaprasad, J. S. Sandhu and J. N. Baruah, Heterocycles, 1983, 20, 787.
31. T. Sasaki, K. Minamoto, T. Suzuki and S. Yamashita, Tetrahedron, 1980, 36, 865.
32. For an intramolecular nitrile oxide and nitrone cycloaddition see: (a) D. Prajapati, P. J. Bhuyan and J. S. Sandhu, J. Chem. Soc., Perkin Trans. 1, 1988, 607;
33. (b) For a report on pyrazolopyrimidine derivatives see: P. J. Bhuyan, R. C. Baruah and J. S. Sandhu, J. Org. Chem., 1990, 55, 568.
34. J. S. Sandhu, S. Mohan and P. S. Sethi, J. Ind. Chem. Soc., 1971, 48, 697.
35. (a) M. Brustlein and T. C. Bruice, J. Am. Chem. Soc., 1972, 94, 6548;
36. (b) S. Shinkai and T. C. Bruice, J. Am. Chem. Soc., 1973, 95, 7526;
37. (c) S. Shinkai, T. Kunitake and T. C. Bruice, J. Am. Chem. Soc., 1974, 96, 7140;
38. (d) M. S. Jorns and L. B. Hersh J. Am. Chem. Soc., 1974, 96, 4012.
39. D. E. O'Brien, L. T. Weinstock and C. C. Cheng, J. Heterocycl. Chem., 1970, 7, 99;
40. F. Yoneda, Y. Sakuma, S. Mizumoto and R. Ito, J. Chem. Soc., Perkin Trans. 1, 1976, 1805.
41. For the hydrazone-azomethine imine tautomerisation by a thermal 1,2-proton shift see; R, Grigg, Chem. Soc. Rev., 1987, 16, 89 and references cited therein.
42. For cycloaddition of a pyrimidine-linked nitrile imine equivalent to an olefin see: M. Noguchi, S. Nagata and S. Kajigaeshi, Chem. Pharm. Bull., 1986, 34, 3994.
43. Thiophene has a lower lying HOMO level than does furan, which increases the energy gap between the interacting FMOs, thereby diminishing the cycloaddition rate. Indeed, this is probably why so little is known about dipolar cycloaddition across thiophene rings see: A. Padwa, D. L. Hertzog and W. R. Nadler, J. Org. Chem., 1994, 59, 7072.
44. P. Caramella, G. Cellerino, K. N. Houk, F. M. Albini and C. Santiago, J. Org. Chem., 1978, 43, 3006;
45. P. Caramella, A. Corsico Coda, A. Corsaro, D. D. Monte and F. M. Albini, Tetrahedron, 1982, 173.
46. A. Hassner, K. S. K. Murthy, A. Padwa, U. Chiacchio, D. C. Dean and A. M. Schoffsfall, J. Org. Chem., 1989, 54, 5277;
47. W. Dehaen and A. Hassner, J. Org. Chem., 1991, 56, 896.
48. For the cycloaddition of hydrazone accelerated by acid catalysts see; B. Fouchet, M. Houch and J. Hameline, Tetrahedron Lett., 1981, 22, 1333;
49. G. Lefevre and J. Hameline, Tetrahedron, 1980, 36, 887;
50. H. Katayama, N. Takatsu, H. Kitano and Y. Shimaya, Chem. Pharm. Bull., 1990, 38, 1129;
51. T. Shimizu, Y. Hayashi, M. Miki and K. Terashima, J. Org. Chem., 1987, 52, 2277.
52. For the oxidation of hydrazone for the generation of nitrile imines see: W. A. F. Gladstone, J. B. Aylward and R. O. C. Norman, J. Chem. Soc. C, 1969, 2587;
53. T. Shimizu, Y. Hayashi, Y. Nagano and K. Teramura, Bull. Chem. Soc. Jpn., 1980, 53, 429.
54. For recent reports see: (a) V. Captar and M. Zinic, Tetrahedron Lett., 1995, 36, 4455;
55. (b) R. Pontikis and C. Monneret, Tetrahedron Lett., 1994, 35, 4351;
56. (c) M. Shionoya, T. Ikeda, E. Kimura and M. Shiro, J. Am. Chem. Soc., 1994, 116, 3848.
57. A. Stein, H. P. Gregor and P. E. Spoerre, J. Am. Chem. Soc., 1956, 78, 6185.