C-C bond formation by radical cyclization: Synthesis of pyrimidine-annulated heterocycles

Synthesis

Volumn , Issue 6, 2003, Pages 920-924

  Majumdar, K C ^a   Mukhopadhyay, P P ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

6 endo trig; Heterocycles; Organotin reagent; Pyrimidine; Radical cyclization

Indexed keywords

CHEMICAL BONDS; NITROGEN; SYNTHESIS (CHEMICAL);

RADICAL CYCLIZATION;

ORGANIC COMPOUNDS;

CARBON; HETEROCYCLIC COMPOUND; PYRIMIDINE; PYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE; RADICAL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; INFRARED RADIATION; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0038367728     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38692     Document Type: Article

References (56)

1. (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: New York, 1986.
2. (b) Curran, D. P. Synthesis 1988, 417.
3. (c) Curran, D. P. Synthesis 1988, 489.
4. (d) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
5. (e) Radicals in Organic Synthesis, Vols. 1 and 2; Renaud, P.; Sibi, M., Eds.; Wiley-VCH: Weinheim, 2001.
6. (f) Majumdar, K. C.; Basu, P. K. Heterocycles 2002, 2413.
7. (a) Ishibashi, H.; Ohata, K.; Niihara, M.; Sato, T.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 2000, 547.
8. (b) Radicals in Organic Synthesis; Renaud, P.; Sibi, M., Eds.; Wiley-VCH: New York 1986.
9. (c) Parsons, A. F.; Williams, D. A. J. Tetrahedron 2000, 56, 7217.
10. (a) Shankaran, K.; Solan, C. P.; Snieckus, V. Tetrahedron Lett. 1985, 26, 6001.
11. (b) Solan, C. P.; Cuevas, J. C.; Quesnelle, C.; Snieckus, V. Tetrahedron Lett. 1988, 29, 4685.
12. (c) Parker, K. A.; Spero, D. M.; Inman, K. C. Tetrahedron Lett. 1986, 27, 2833.
13. (d) Jones, K.; Willkinson, J. A. J. Chem. Soc., Chem. Commun. 1992, 1767.
14. (a) Snieckus, V. Bull. Soc. Chim. Fr. 1988, 67.
15. (b) Harrowven, D. C. Tetrahedron Lett. 1993, 34, 5653.
16. (c) Harrowven, D. C.; Browne, R. Tetrahedron Lett. 1994, 35, 5301.
17. (a) Tsuge, O.; Hatta, T.; Tsuchiyama, H. Chem. Lett. 1998, 155.
18. (b) Fiumana, A.; Jones, K. Tetrahedron Lett. 2000, 41, 4209.
19. (c) Sundberg, R. J.; Cherney, R. J. J. Org. Chem. 1990, 55, 6028.
20. (a) Rosa, A. M.; Prabhakar, S.; Lobo, A. M. Tetrahedron Lett. 1990, 13, 1881.
21. (b) Rosa, A. M.; Lobo, A. M.; Branco, P. S.; Prabhakar, S.; Pereira, A. M. D. L. Tetrahedron 1997, 55, 269.
22. Ishibashi, H.; Kato, I.; Takeda, Y.; Kogure, M.; Tamura, O. Chem. Commun. 2000, 1527.
23. Ponaras, A. A.; Zaim, O. Tetrahedron Lett. 2000, 41, 2279.
24. Cid, M. M.; Dominguez, D.; Castedo, L.; Va'zquez-Lopez, E. M. Tetrahedron 1999, 55, 5599.
25. Heidelberger, C. In Pyrimidine and Pyrimidine Antimetabolites in Cancer Medicine; Holland, J. F.; Frei, E., Eds.; Lea and Febiger: Philadelphia, 1984, 801.
26. DeClercq, E.; Descamps, J.; Somer, P. De; Barr, P. J.; Jones, A. S.; Walker, R. T. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 2947.
27. Heidelberger, C.; King, D. H. Antiviral Agents in Pharmacology and Therapeutics, Vol. 6; Shugar, D., Ed.; Pergamon: Oxford, 1979, 427.
28. Mitsuya, H.; Weinhold, K. J.; Furman, P. A.; St. Clair, M. H.; Lehrman, S. N.; Gallo, R. C.; Bolognesi, D.; Barry, D. W.; Broder, S. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 7096.
29. Fischl, M. A.; Richman, D. D.; Grieco, M. H.; Gottlieb, M. S.; Volberdin, P. A.; Laskin, O. L.; Leedom, J. M.; Groopman, J. E.; Mildvan, D.; Schooley, R. T.; Jackson, G. G.; Durack, D. T.; King, D. N. Engl. J. Med. 1987, 317, 185.
30. (a) MacIlwain, C. Nature (London) 1993, 365, 378.
31. (b) Gallo, R. C. Sci. Am. 1986, 255, 78. (c) Gallo, R. C. Sci. Am. 1987, 256, 38.
32. (c) Gallo, R. C. Sci. Am. 1987, 256, 38.
33. Griengl, H.; Bodenteich, M.; Hayden, W.; Wanek, E.; Streicher, W.; Stutz, P.; Bachmayer, H.; Ghazzo-uli, I.; Rosenwirth, B. J. Med. Chem. 1985, 28, 1679.
34. DeClercq, E.; Descamps, J.; Ogata, M.; Shigeta, S. Antimicrob. Agents Chemother. 1982, 21, 33.
35. DeClercq, E.; Rosenwirth, B. Antimicrob. Agents Chemother. 1985, 28, 246.
36. Rosenwirth, B.; Griengl, H.; Wanek, E.; DeClercq, E. Antiviral Res. 1985, Suppl. I, 21.
37. Miyasaka, T.; Tanaka, H.; Baba, M.; Hayakawa, H.; Walker, R. T.; Balzarini, J.; DeClercq, E. J. Med. Chem. 1989, 32, 2507.
38. Baba, M.; Tanaka, H.; DeClercq, E.; Pauwels, R.; Balzarini, J.; Schols, D.; Nakashima, H.; Perno, C. F.; Walker, R. T.; Miyasaka, T. Biochem. Biophys. Res. Commun. 1989, 165, 1375.
39. DeClercq, E. Medicinal Res. Rev. 1993, 13, 229.
40. Kundu, N. G.; Das, P. J. Chem. Soc., Chem. Commun. 1995, 99.
41. Botta, M.; Saladino, R.; Lamba, D.; Nicoletti, R. Tetrahedron 1993, 49, 6053.
42. Kundu, N. G.; Dasgupta, S. K. J. Chem. Soc., Perkin Trans. 1 1993, 2657.
43. (a) Majumdar, K. C.; Das, U. J. Org. Chem. 1998, 63, 9997.
44. (b) Majumdar, K. C.; Das, U. J. Chem. Res., Synop. 1997, 309.
45. (c) Majumdar, K. C.; Das, U. J. Chem. Res., Miniprint 1997, 2062.
46. (d) Majumdar, K. C.; Das, U. Synth. Commun. 1997, 27, 4013.
47. (e) Majumdar, K. C.; Das, U.; Jana, N. K. J. Org. Chem. 1998, 63, 3550.
48. Majumdar, K. C.; Mukhopadhyay, P. P. Synthesis 2003, 97.
49. Ishibashi, H.; Kawanami, H.; Nakagawa, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1997, 2291.
50. Abeywickrema, A. N.; Beckwith, A. L. J.; Gerba, S. J. Org. Chem. 1987, 52, 4072.
51. (a) Rosa, A. M.; Lobo, A. M.; Branco, P. S.; Prabhakar, S.; Sa-da-Costa, S. M. Tetrahedron 1997, 53, 299.
52. (b) Aldabbagh, F.; Bowman, W. R. Tetrahedron Lett. 1997, 38, 3793.
53. (c) Curran, D. P.; Ko, S.-B.; Josien, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2683.
54. (d) Bowman, W. R.; Cloonan, M. O.; Krintel, S. L. J. Chem. Soc., Perkin Trans. 1 2001, 2885.
55. (e) Bowman, W. R.; Mann, E.; Parr, J. J. Chem. Soc., Perkins Trans. 1 2000, 2991.
56. (f) Comins, D.L.; Hong, H.; Jianhua, G. Tetrahedron Lett. 1994, 35, 5331.