Regioselective synthesis of 1H,3H,6H[2]benzopyrano[4,3-d]pyrimidine-2,4-diones and 12H-benzopyrano[3,2-c][1]benzopyran-5-ones by radical cyclization

Tetrahedron

Volumn 59, Issue 12, 2003, Pages 2151-2157

  Majumdar, K C ^a   Basu, P K ^a   Mukhopadhyay, P P ^a   Sarkar, S ^a   Ghosh, S K ^a   Biswas, P ^a  

^a UNIVERSITY OF KALYANI   (India)

Author keywords

2 bromobenzyl bromide; Azobisisobutyronitrile; Radical cyclization; Sodium cyanoborohydride; Tri n butyltin chloride

Indexed keywords

5 (2' BROMOBENZYLOXY)PYRIMIDINE 2,4 DIONE; BENZOPYRAN DERIVATIVE; BROMIDE; KETONE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0037451003     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00182-0     Document Type: Article

References (55)

1. (a) Giese B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds. 1986;Pergamon, New York
2. (b) Curran D.P. Synthesis. 1988;417. see also pp 489
3. (c) Jasperse C.P., Curran D.P., Fevig T.L. Chem. Rev. 91:1991;1237.
4. Majumdar K.C., Balasubramanium K.K., Thyagarajan B.S. J. Heterocycl. Chem. 10:1973;159.
5. Majumdar K.C., Das U. J. Org. Chem. 63:1998;9997.
6. (a) Majumdar K.C., Chatterjee P., Saha S. Tetrahedron Lett. 39:1998;7147
7. (b) Majumdar K.C., Chatterjee P., Saha S., Samanta S.K. Indian J. Chem. 40B:2001;915.
8. (a) Shankaran K., Solan C.P., Snieckus V. Tetrahedron Lett. 26:1985;6001
9. (b) Solan C.P., Cuevas J.C., Quesnelle C., Snieckus V. Tetrahedron Lett. 29:1988;4685
10. (c) Parker K.A., Spero D.M., Inman K.C. Tetrahedron Lett. 27:1986;2833
11. (d) Jones K., Willkinson J.A. J. Chem. Soc., Chem. Commun. 1992;1767.
12. (a) Snieckus V. Bull. Soc. Chim. Fr. 1988;67
13. (b) Harrowven D.C. Tetrahedron Lett. 34:1993;5653
14. (c) Harrowven D.C., Browne R. Tetrahedron Lett. 35:1994;5301.
15. Sundberg R.J., Cherney R.J. J. Org. Chem. 55:1990;6028.
16. Rosa A.M., Prabhakar S., Lobo A.M. Tetrahedron Lett. 13:1990;1881.
17. Ishibashi H., Kato I., Takeda Y., Kogure M., Tamura O. Chem. Commun. 2000;1527.
18. Ponaras A.A., Zaim O. Tetrahedron Lett. 41:2000;2279.
19. Cid M.M., Dominguez D., Castedo L., Va'zquez-Lopez E.M. Tetrahedron. 55:1999;5599.
20. Heidelberger C. Holland J.F., Frei E. Pyrimidine and Pyrimidine Antimetabolites in Cancer Medicine. 1984;801 Lea and Febiger, Philadelphia.
21. DeClercq E., Descamps J., Somer P.D., Barr P.J., Jones A.S., Walker R.T. Proc. Natl Acad. Sci. USA. 76:1979;2947.
22. Heidelberger C., King D.H. Shugar D. Antiviral Agents in Pharmacology and Therapeutics. Vol. 6:1979;427 Pergamon, Oxford.
23. 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. USA. 82:1985;7096.
24. 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. N. Engl. J. Med. 317:1987;185.
25. Griengl H., Bodenteich M., Hayden W., Wanek E., Streicher W., Stutz P., Bachmayer H., Ghazzo-uli I., Rosenwirth B. J. Med. Chem. 28:1985;1679.
26. DeClercq E., Descamps J., Ogata M., Shigeta S. Antimicrob. Agents Chemother. 21:1982;33.
27. DeClercq E., Rosenwirth B. Antimicrob. Agents Chemother. 28:1985;246.
28. Rosenwirth B., Griengl H., Wanek E., DeClercq E. Antiviral Res. Suppl. I:1985;21.
29. MacIlwain C. Nature. 365:1993;378.
30. (a) DeClercq E., Balzarini J., Torrence P.F., Mertes M.P., Schmidt C.L., Shugar D., Barr P.J., Jones A.S., Verhelst G., Walker R.T. Mol. Pharmacol. 19:1981;321
31. (b) Danenberg V., Bhatt R.S., Kundu N.G., Danenberg K., Heidelberger C. J. Med. Chem. 24:1981;1537
32. (c) Chu C.K., Schinagi R.F., Ahn M.K., Ulas G.V., Gu Z.P. J. Med. Chem. 32:1989;612.
33. (a) Prober J.M., Trainer G.L., Dam R.J., Hobbs F.W., Robertson C.W., Zagursky R.J., Cocuzza A.J., Jehnsen M.A., Banmeister K. Science. 238:1987;336
34. (b) Povsic T.J., Dervan P.B. J. Am. Chem. Soc. 112:1990;9428.
35. Miyasaka T., Tanaka H., Baba M., Hayakawa H., Walker R.T., Balzarini J., DeClercq E. J. Med. Chem. 32:1989;2507.
36. 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. 165:1989;1375.
37. DeClercq E. Med. Res. Rev. 13:1993;229.
38. (a) Gallo R.C. Sci. Am. 255:1986;78
39. (b) Gallo R.C. Sci. Am. 256:1987;38.
40. Kundu N.G., Das P. J. Chem. Soc., Chem. Commun. 1995;99.
41. Botta M., Saladino R., Lamba D., Nicoletti R. Tetrahedron. 49:1993;6053.
42. Kundu N.G., Dasgupta S.K. J. Chem. Soc., Perkin Trans 1. 1993;2657.
43. (a) Majumdar K.C., Das U. J. Chem. Res. (S). 1997;309
44. (b) Majumdar K.C., Das U. J. Chem. Res. (M). 1997;2062.
45. Majumdar K.C., Das U. Synth. Commun. 27:1997;4013.
46. Majumdar K.C., Das U., Jana N.K. J. Org. Chem. 63:1998;3550.
47. (a) Feur G. Ellis G.P., West G.B. Progress in Medicinal Chemistry. 1974;North-Holland, New York
48. (b) Lauger V.P., Martin H., Muller P. Helv. Chim. Acta. 27:1994;892
49. (c) Soine T. J. Pharm. Sci. 53:1964;231.
50. Ishibashi H., Kawanami H., Nakagawa H., Ikeda M. J. Chem. Soc., Perkin Trans. 1. 1997;2291.
51. Abeywickrema A.N., Beckwith A.L.J., Gerba S. J. Org. Chem. 52:1987;4072.
52. (a) Rosa A.M., Lobo A.M., Branco P.S., Prabhakar S., Sa-da-Costa S.M. Tetrahedron. 53:1997;299
53. (b) Aldabbagh F., Bowman W.R. Tetrahedron Lett. 38:1997;3793
54. (c) Curran D.P., Ko S.-B., Josien H. Angew. Chem. Int. Ed. Engl. 34:1995;2683
55. (d) Bowman W.R., Cloonan M.O., Krintel S.L. J. Chem. Soc., Perkin Trans. 1. 2001;2885.