Ring transformation of unsaturated N -bridgehead fused pyrimidin-4(3 H)-ones: Role of repulsive electrostatic nonbonded interaction

Journal of Organic Chemistry

Volumn 76, Issue 2, 2011, Pages 696-699

  Molnár, Annamária ^a,b   Mucsi, Zoltán ^b   Vlád, Gábor ^a   Simon, Kálmán ^a   Holczbauer, Tamás ^c   Podányi, Benjámin ^a   Faigl, Ferenc ^b   Hermecz, István ^b  

^a Chinoin Pharmaceutical and Chemical Works Ltd   (Hungary)

^b BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

^c CHEMICAL RESEARCH CENTER   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYL GROUPS; ELECTROSTATIC INTERACTIONS; ELECTROSTATIC NONBONDED INTERACTIONS; RING TRANSFORMATION;

OXYGEN;

ELECTROSTATICS;

CARBONYL DERIVATIVE; HETEROCYCLIC KETONE; NITROGEN; NITROGEN BRIDGEHEAD FUSED PYRIMIDIN 4(3H) ONE DERIVATIVE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CYCLIZATION; STATIC ELECTRICITY;

CYCLIZATION; CYCLOPARAFFINS; HETEROCYCLIC COMPOUNDS, 2-RING; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PYRIMIDINONES;

EID: 78651509934     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102079k     Document Type: Article

References (46)

1. Johnson, E. R.; Keinan, B.; Mori-Sánchez, P.; Contreras-Garcia, J.; Cohen, A. J.; Yang, W. J. Am. Chem. Soc. 2010, 132, 6498
2. Kollman, P. A. Acc. Chem. Res. 1977, 10, 365
3. Pozgan, F.; Kocevar, M. Heterocycles 2009, 77, 657
4. van der Plas, H. C. ARKIVOC 2008, iii) 127
5. van der Plas, H. C. Adv. Heterocycl. Chem. 2003, 84, 31
6. van der Plas, H. C Adv. Heterocycl. Chem. 1999, 74, 1
7. Wermuth, C. G. Ring Transformations 239. In Practice of Medicinal Chemistry; Wermuth, C. G., Ed.; Academic Press: London, 1996.
8. Paetzel, M.; Liebschen, J. Synthesis 1995, 879
9. Vivona, N.; Buscemi, S.; Frenna, V.; Gusmano, G. Adv. Heterocycl. Chem. 1993, 56, 49
10. van der Plas, H. C. Tetrahedron 1985, 41, 237
11. van der Plas, H. C. Arom. Heteroarom. Chem. 1977, 4, 163
12. van der Plas, H. C. Arom. Heteroarom. Chem. 1976, 3, 146
13. van der Plas, H. C. Ring transformations of heterocycles. Vols 1 & 2. In Organic Chemistry: A series of Monographs; Blomquist, A. T., Ed.; Academic Press: New York, 1973; Vol. 27.
14. Di Micco, S.; Vitale, R.; Pellecchia, M.; Rega, M. F.; Riva, R.; Basso, A.; Bifulco, G. J. Med. Chem. 2009, 52, 7856
15. Gangjee, A.; Jain, H. D.; Queener, S. F.; Kisliuk, R. L. J. Med. Chem. 2008, 51, 4589
16. Nawrot-Modranka, J.; Nawrot, E.; Graczyk, J. Eur. J. Med. Chem. 2008, 51, 1301
17. Sharon, A.; Pratap, R.; Tiwari, P.; Srivastava, A.; Maulik, P. R.; Ram, V. J. Bioorg. Med. Chem. Lett. 2005, 15, 2115
18. Sharon, A.; Pratap, R.; Tripathi, B.; Srivastava, A.; Maulik, P. R.; Ram, V. J. Bioorg. Med. Chem. Lett. 2005, 15, 1341
19. Farhanullah; Tripathi, B. K.; Srivastava, A.; Ram, V. J. Bioorg. Med. Chem. 2004, 12, 1543
20. Hermecz, I.; Keresztúri, G.; Vasvári-Debreczy, L. Adv. Heterocycl. Chem. 1992, 54, 215
21. Hermecz, I.; Vasvári-Debreczy, L.; Simon, K. J. Chem. Soc., Perkin Trans. 2 1988, 1287
22. Hermecz, I.; Mészáros, Z.; Simon, K.; Szabó, L.; Pál, Z. J. Chem. Soc., Perkin Trans. 1 1984, 1795
23. Hermecz, I.; Mészáros, Z.; Vasvári-Debreczy, L.; Horváth, Á.; Horváth, G.; Pongor-Csákvári, M. J. Chem. Soc., Perkin Trans. 1 1977, 789
24. Lesher, G. Y.; Froechlich, E. J.; Gruett, M. D.; Bailey, J. H.; Brundage, R. P. J. Med. Chem. 1962, 5, 1063
25. Lesher, G. Y. Int. Congr. Chemother. Proc 2 1964, 1367
26. Wise, R.; J. Andrews, M.; Edwards, L. J. Antimicrob. Agents Chemother. 1983, 23, 559
27. Mitscher, L. A.; Sharma, P. N.; Chu, D. T. W.; Shen, L. L.; Pernet, A. G. J. Med. Chem. 1987, 30, 2283
28. Lappin, G. R. J. Am. Chem. Soc. 1948, 70, 3348
29. Mészáros, Z.; Hermecz, I. Tetrahedron Lett. 1975, 14, 1019
30. Chen, K.; Kuo, S.-C.; Hsieh, M.-C.; Mauger, A.; Lin, C. M.; Hamel, E.; Lee, K.-H. J. Med. Chem. 1997, 40, 2266
31. Chen, K.; Kuo, S.-C.; Hsieh, M.-C.; Mauger, A.; Lin, C. M.; Hamel, E.; Lee, K.-H. J. Med. Chem. 1997, 40, 3049
32. Zhang, S.-X.; Bastow, K. F.; Tachibana, Y.; Kuo, S.-C.; Hamel, E.; Mauger, A.; Narayanan, V. L.; Lee, K.-H. J. Med. Chem. 1999, 42, 4081
33. Hermecz, I. Adv. Heterocycl. Chem. 2003, 85, 173
34. Carboni, S.; Da Settimo, A.; Ferrarini, P. L.; Livi, O. Farmaco Ed. Sci. 1978, 33, 315.
35. D'Andrea, S. US Patent Appl. 2008/0107625.
36. Plüg, C.; Wallfisch, B.; Andersen, H. G.; Bernhardt, P. V.; Baker, L.-J.; Clark, G. R.; Wong, M. W.; Wentrup, C. J. Chem. Soc., Perkin Trans. 2 2000, 2096
37. Molnár, A.; Faigl, F.; Podányi, B.; Finta, Z.; Balázs, L.; Hermecz, I. Heterocycles 2009, 78, 2477
38. Lesher, G. Y. U.S. Patent 3,907,798, 1975.
39. 2O for 5 min gave 80% of 5,7-dimethyl-1,8-naphthyridin-4-one. When we repeated the experiment 6,8-dimethyl-4 H -pyrido[1,2-a ]pyrimidin-4-one was the main product, in agreement with the result of Lesher. (13) After a reaction of time 5 h, the amounts of pyridopyrimidinone and 1,8-naphthyridinone were nearly equal. Da Silva, L. E.; Joussef, A. C.; Nunes, R. J.; de Oliveira, K. N. Synth. Commun. 2008, 38, 15
40. Charlton, M. J. Am. Chem. Soc. 1975, 97, 1552
41. Chein, R. J.; Corey, E. J. Org. Lett. 2010, 12, 132
42. Ballesteros-Garrido, R.; Blanco, F.; Ballesteros, R.; Leroux, F. R.; Abarca, B.; Colobert, F.; Alkorta, I.; Elguero, J. Eur. J. Org. Chem. 2009, 5765
43. Ferrarini, P. L.; Mori, C.; Manera, C.; Martinelli, A.; Mori, F.; Saccomanni, G.; Barili, P. L.; Betti, L.; Giannaccini, G.; Trincavelli, L.; Lucacchini, A. J. Med. Chem. 2000, 43, 2814
44. Fourmigué, M. Curr. Opin. Solid State Mater. Sci. 2009, 13, 36
45. Palusiak, M.; Grabowski, S. J. Struct. Chem. 2008, 19, 5
46. Metrangolo, P.; Neukirch, H.; Pilati, T.; Resnati, G. Acc. Chem. Res. 2005, 38, 386