Synthesis of purine- and pyrimidine-substituted heptadienes. The stereochemistry of cyclization and cyclopolymerization products

Journal of Organic Chemistry

Volumn 68, Issue 4, 2003, Pages 1235-1241

  Tsai, Jui Yi ^a,b   Bouhadir, Kamal Hani ^a   Zhou, Jing Lan ^a   Webb, Thomas R ^a   Sun, Yahong ^a   Shevlin, Philip B ^a  

^a AUBURN UNIVERSITY   (United States)

^b PPG INDUSTRIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONDENSATION; COPOLYMERS; DERIVATIVES; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

CYCLIZATION;

NUCLEIC ACIDS;

1,6 HEPTADIEN 4 OL; 1,6 HEPTADIENE; ADENINE DERIVATIVE; ALKADIENE; CARBON TETRACHLORIDE; COPOLYMER; CYTOSINE DERIVATIVE; FREE RADICAL; GUANINE DERIVATIVE; NUCLEIC ACID BASE; PURINE; PYRIMIDINE; THYMINE DERIVATIVE; TRIAZOLE; UNCLASSIFIED DRUG; URACIL; URACIL DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; ISOMERISM; MITSUNOBU REACTION; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; STEREOCHEMISTRY; STEREOSPECIFICITY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0037458990     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026379k     Document Type: Article

References (50)

1. (a) Schuster, M. J.; Wu, G. Y. Drugs Today 1996, 32, 653-661.
2. (b) Sanghvi, Y. S.; Cook, P. D. In Nucleotides and Nucleosides as Antitumor and Antiviral Agents; Chu, C. K., Baker, D. C., Eds.; Plenum: New York, 1993; pp 311-324.
3. (c) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745-1768.
4. (d) Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 544.
5. (e) Smith, W. T. Prog. Polym. Sci. 1996, 21, 209-253.
6. (f) Takemoto, K.; Mochizuki, E.; Wada, T.; Inaki, Y. Biomimetic Polym. 1990, 253.
7. (a) Geise, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press: Oxford, 1986.
8. (b) De Riggi, S. G.; Surzur, J. M.; Bertrand, M. P. J. Org. Chem. 1992, 57, 6118-6125.
9. (c) Brumwell, J. E.; Simpkins, N. S. Tetrahedron Lett. 1993, 34 (7), 1219-1222.
10. (d) Naim, A.; Mills, G.; Shevlin, P. B. Tetrahedron Lett. 1992, 33 (45), 6779-6782.
11. (a) Butler, G. B. Cyclopolymerization and Cyclocopolymerization; Marcel Dekker Inc.: New York, 1992; Chapter 2.
12. (b) Amemiya, Y.; Katayama, M.; Harada, S. Makromol. Chem. 1977, 178, 2499-2505.
13. (a) Huang, Z.; Schneider, K. C.; Benner, S. A. J. Org. Chem. 1991, 56, 3869-3882.
14. (b) Baseschlin, D. K.; Hyrup, B.; Benner, S. A.; Richert, C. J. Org. Chem. 1996, 61, 7620-7626.
15. (c) Schneider, K. C.; Benner, S. A. Tetrahedron Lett. 1990, 31 (3), 335-338.
16. (d) Jenny, T. F.; Benner, S. A. Helv. Chim. Acta 1993, 76, 826-841.
17. Roughton, A. L.; Portmann, S.; Benner, S. A.; Egli, M. J. Am. Chem. Soc. 1995, 117, 7249-7250.
18. Hyrup, B.; Richert, C.; Schulte-Herbruggen, T.; Benner, S. A.; Egli, M. Nucleic Acids Res. 1995, 117, 7249-7250.
19. (a) Beckwith, A. L. J.; Blair, I.; Phillipou, G. J. Am. Chem. Soc. 1974, 96, 1613-1614.
20. (b) Beckwith, A. L. J.; Lawrence, T.; Serelis, A. K. J. Chem. Soc., Chem. Commun. 1980, 484-485.
21. (c) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41 (19), 3925-3941.
22. (d) Kuehne, M. E.; Damon, R. E. J. Org. Chem. 1977, 42, 1825-1832.
23. (e) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron Lett. 1985, 26 (3), 373-376.
24. (f) Beckwith, A. L. J.; Easton, C. J.; Lawrence, T.; Serelis, A. K. Aust. J. Chem. 1983, 36, 545-556.
25. (a) Jenny, T. F.; Benner, S. A. Tetrahedron Lett. 1992, 33 (44), 6619-6620.
26. (b) Jenny, T. F.; Previsani, N.; Benner, S. A. Tetrahedron Lett. 1991, 32 (48), 7029-7032.
27. Jenny, T. F.; Schneider, K. C.; Benner, S. A. Nucleosides Nucleotides 1992, 11 (6), 1257-1261.
28. Schulhof, J. C.; Molko, D.; Teoule, R. Tetrahedron Lett. 1987, 28, 51-54.
29. Brown, D. M.; Todd, A.; Varadarajan, S. J. Chem. Soc. 1956, 2384-2387.
30. Perez-Perez, M. J.; Rozenski, J.; Busson, R.; Herdewijn, P. J. Org. Chem. 1995, 60, 1531-1537.
31. Hossian, N.; Rozenski, J.; Clercq, E. D.; Herdewijn, P. Tetrahedron 1996, 43, 13655-13670.
32. Bonnal, C.; Chavis, C.; Lucas, M. J. Chem. Soc., Perkin Trans. 1 1994, 11, 1401-1410.
33. Zhou, J.-L. Ph.D. Thesis, Auburn University, Auburn, AL, 1997.
34. Divakar, K. J.; Reese, C. B. J. Chem. Soc., Perkin Trans. 1 1982, 1171-1176.
35. Inaki, Y.; Fukunaga, S.; Suda, Y.; Takemoto, K. J. Polym. Sci., Polym. Chem. Ed. 1985, 24, 119-132.
36. Gajewski, J. J.; Gilbert, K. E.; McKelvey, J. In Advances in Molecular Modelling; Liotta, D. A., Ed.; JAI Press: Greenwhich, CT, 1990; Vol. 2, p 65. The program used was PCWIN, version 5.1, from Serena Software, Bloomington, IN.
37. Asscher, M.; Vofsi, D. Org. Synth. 1965, 45, 104-107.
38. (a) McLean, C. D.; Ong, A. K.; Solomon, D. H. J. Macromol. Sci., Chem. 1976, 10, 857-873.
39. (b) Dixon, W. T.; Norman, R. O. C.; Buley, A. L. J. Chem. Soc. 1964, 3625-3634.
40. Dainton, F. S.; Ivin, K. J. Trans. Faraday Soc. 1950, 46, 331-348.
41. (a) Frey, F. E. J. Am. Chem. Soc. 1943, 65, 2417-2418.
42. (b) Bywater, S. Trans. Faraday Soc. 1955, 51, 1267-1272.
43. (c) Ivin, K. J. Trans. Faraday Soc. 1955, 51, 1273-1279.
44. Mazzolini, C.; Patron, L.; Moretti, A.; Campanelli, M. Ind. Eng. Chem. Prod. Res. Dev. 1970, 9 (4), 504-511.
45. Butler, G. B. Cyclopolymerization and Cyclocopolymerization; Marcel Dekker: New York, 1992; Chapter 2, p 39.
46. Lancaster, J.; Baccei, L.; Panzer, H. J. Polym. Sci., Polym. Lett. Ed. 1976, 14, 549-554.
47. Gambino, J.; Yang, T. F.; Wright, G. E. Tetrahedron 1994, 50 (39), 11363-11368.
48. For an explanation for the lack of degradative chain transfer on the monomer 6, see: Kabanov, V. A.; Topchiev, D. A.; Nazhmetdinova, G. T. Vysokomol. Soedin., Ser. B 1984, 26 (1), 51-53.
49. Lancaster, J.; Baccei, L.; Panzer, H. J. Polym. Sci., Polym. Lett Ed. 1976, 14, 549-554.
50. Barbot, F. J. Organomet. Chem. 1977, 132, 445-454.