H-bond-assisted intramolecular nucleophilic displacement of the 1-NMe 2 group in 1,8-bis(dimethylamino)naphthalenes as a route to multinuclear heterocyclic compounds and strained naphthalene derivatives

Journal of Organic Chemistry

Volumn 76, Issue 17, 2011, Pages 7157-7166

  Povalyakhina, Maria A ^a   Antonov, Alexander S ^a   Dyablo, Olga V ^a   Ozeryanskii, Valery A ^a   Pozharskii, Alexander F ^a  

^a SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

AZOMETHINES; CARBONYL DERIVATIVES; HETEROCYCLIC COMPOUND; HETEROCYCLIZATIONS; HIGH YIELD; HYDRAZONES; INDAZOLE; ISOXAZOLES; LEAVING GROUPS; NAPHTHALENE DERIVATIVES; NUCLEOPHILIC DISPLACEMENT; PROTON SPONGE; PROTONATED; QUINAZOLINES;

PHENOLS;

NAPHTHALENE;

1 NAPHTHOL DERIVATIVE; 1,8 DIS(DIMETHYLAMINO)NAPHTHALENE DERIVATIVE; 8 DIMETHYLAMINO 1 NAPHTHOL; BENZO[G]INDAZOLE; BENZO[G]QUINAZOLINE; HETEROCYCLIC COMPOUND; INDAZOLE DERIVATIVE; ISOXAZOLE DERIVATIVE; NAPHTHALENE DERIVATIVE; NAPHTHO[2,1 DEXTRO]ISOXAZOLE; PROTON; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; HYDROGEN BOND; NUCLEOPHILICITY;

EID: 80052174323     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201171z     Document Type: Article

References (44)

1. Alder, R. W.; Bowman, P. S.; teele, W. R. S.; Winterman, D. R. J. Chem. Soc., Chem. Commun. 1968, 723
2. Pietrzak, M.; Wehling, J.; Limbach, H. H.; Golubev, N. S.; Lopez, C.; Claramunt, R. M.; Elguero, J. J. Am. Chem. Soc. 2001, 123, 4338
3. Perrin, C. L.; Ohta, B. K. J. Am. Chem. Soc. 2001, 123, 6520
4. Pozharskii, A. F.; Ozeryanskii, V. A. Russ. Chem. Bull. 1998, 47, 66
5. Malarski, Z.; Sobczyk, L; Grech, E. J. Mol. Struct. 1988, 177, 339
6. Howard, S. T. J. Am. Chem. Soc. 2000, 122, 8238
7. Hodgson, P.; Lloyd-Jones, G. C.; Murray, M.; Peakman, T. M.; Woodward, R. L. Chem.. - Eur. J. 2000, 6, 4451
8. Degtyarev, A. V.; Ryabtsova, O. V.; Pozharskii, A. F.; Ozeryanskii, V. A.; Starikova, Z. A.; Sobczyk, L; Filarowski, A. Tetrahedron 2008, 64, 6209
9. Hibbert, F. Acc. Chem. Res. 1984, 17, 115
10. Hibbert, F. Adv. Phys. Org. Chem. 1986, 22, 113
11. Toppet, S.; Platteborze, K.; Zeegers-Huyskens, T. J. Chem. Soc., Perkin Trans. 2 1995, 831
12. Benoit, R. L.; Lefebvre, D.; Frechette, M. Can. J. Chem. 1987, 65, 996
13. de Groot, R. L.; Sikkema, D. J. J. R. Neth. Chem. Soc. 1976, 95, 10
14. Staab, H. A.; Saupe, T. Angew. Chem., Int. Ed. Engl. 1988, 27, 865
15. Alder, R. W. Chem. Rev. 1989, 89, 1215
16. Pozharskii, A. F. Russ. Chem. Rev. 1998, 67, 1
17. Pozharskii, A. F.; Ozeryanskii, V. A. In The Chemistry of Anilines; Rappoport, Z., Ed.; J. Wiley & Sons: Chichester, 2007; Part 2, Chapter 17, p 931.
18. Llamas-Saiz, A. L.; Foces-Foces, C.; Elguero, J. J. Mol. Struct. 1994, 328, 297
19. Sobzyk, L.; Grabowskii, S. J.; Krygowskii, T. M. Chem. Rev. 2005, 105, 3513
20. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Book: Sausalito, CA, 2006; p 179.
21. Kurasov, L. A.; Pozharskii, A. F.; Kuz'menko, V. V.; Klyuev, N. A.; Chernyshev, A. I.; Goryaev, S. S.; Chikina, N. L. Zh. Org. Khim. 1983, 19, 590
22. Chem. Abstr. 1983, 99, 22064v.
23. Alder, R. W.; Anderson, J. E. J. Chem. Soc., Perkin Trans. 2 1973, 2086
24. Reich, H. J.; Cohen, M. L. J. Org. Chem. 1979, 44, 3148
25. Ozeryanskii, V. A.; Pozharskii, A. F.; Koroleva, M. G.; Shevchuk, D. A.; Kazheva, O. N.; Chekhlov, A. N.; Shilov, G. V.; Dyachenko, O. A. Tetrahedron 2005, 61, 4221
26. Pozharskii, A. F.; Degtyarev, A. V.; Ryabtsova, O. V.; Ozeryanskii, V. A.; Kletskii, M. E.; Starikova, Z. A.; Sobczyk, L.; Filarowski, A. J. Org. Chem. 2007, 72, 3006
27. Mallinson, P. R.; Smith, G. T.; Wilson, C. C.; Grech, E.; Wozniak, K. J. Am. Chem. Soc. 2003, 125, 4259
28. Elguero, J.; Cano, F. H.; Foces-Foces, C.; Llamas-Saiz, A. L.; Limbach, H.-H.; Aguilar-Parrilla, F.; Claramunt, R. M.; López, C. J. Heterocycl. Chem. 1994, 31, 695
29. Albert, A. In Physical Methods in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: New York, 1963; Chapter 1.
30. 3N: Dale, T. G.; Sather, A. C.; Rebek, J., Jr. Tetrahedron Lett. 2009, 50, 6173
31. Katritzky, A. R.; Pozharskii, A. F. Handbook of Heterocyclic Chemistry; Pergamon: Amsterdam, 2000; p 412.
32. Pozharskii, A. F.; Ozeryanskii, V. A.; Kuz'menko, V. V. Russ. J. Org. Chem. 1996, 32, 66
33. Hojo, M.; Masuda, R.; Okada, E.; Mija, H. Synthesis 1989, 870
34. Infantes, L.; Motherwell, S. Struct. Chem. 2004, 15, 173
35. Shmidt, E. Yu.; Mikhaleva, A. I.; Zorina, N. V.; Kazheva, O. N.; Shilov, G. V.; D'yachenko, O. A.; Trofimov, B. A. Doclady Chemistry, 2008, 421, 197.
36. Blanco, F.; Alkorta, I.; Elguero, J. Croat. Chem. Acta 2009, 82, 173
37. Pozharskii, A. F.; Ryabtsova, O. V.; Ozeryanskii, V. A.; Degtyarev, A. V.; Starikova, Z. A.; Sobczyk, L.; Filarowski, A. Tetrahedron Lett. 2005, 46, 3973
38. Ozeryanskii, V. A.; Milov, A. A.; Minkin, V. I.; Pozharskii, A. F. Angew. Chem., Int. Ed. 2006, 45, 1453
39. Pozharskii, A. F.; Ryabtsova, O. V.; Ozeryanskii, V. A.; Degtyarev, A. V.; Kazheva, O. N.; Alexandrov, G. G.; Dyachenko, O. A. J. Org. Chem. 2003, 68, 10109
40. Benoit, R. L.; Lefebvre, D.; Frechette, M. Can. J. Chem. 1987, 65, 996
41. Kirsch, A.; Krieger, C.; Staab, H. A.; Neugebauer, F. A. Tetrahedron Lett. 1994, 35, 8365
42. Albert, A.; Serjeant, E. P. Ionization Constants of Acids and Bases, 2 nd ed.; Chapman and Hall: London, 1971.
43. Kirby, A. J.; Davies, J. E.; Fox, D. J.; Hodgsob, D. R. W.; Goeta, A. E.; Lima, M. F.; Priebe, J. P.; Santaballa, J. A.; Nome, F. Chem. Commun. 2010, 46, 1302
44. Grammaticakis, P. Bull. Soc. Chim. Fr. 1953, 20, 93