N,N,N′-Trialkyl-1,8-diaminonaphthalenes: Convenient method of preparation from protonated proton sponges and the first X-ray information

Tetrahedron

Volumn 61, Issue 17, 2005, Pages 4221-4232

  Ozeryanskii, V A ^a   Pozharskii, A F ^a   Koroleva, M G ^a   Shevchuk, D A ^a   Kazheva, O N ^b   Chekhlov, A N ^b   Shilov, G V ^b   Dyachenko, O A ^b  

^a SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

^b INSTITUTE OF PROBLEMS OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

Dealkylation; Demethylation; Intramolecular hydrogen bond; Molecular and crystal structures; N,N,N Trialkyl 1,8 diaminonaphthalenes; Nitronaphthalenes; Proton sponges; Realkylation

Indexed keywords

1 DIMETHYLAMINO 8 METHYLAMINO 4 NITRONAPHTHALENE; 8 DIMETHYLAMINO 1 METHYLAMINO 4 NITRONAPHTHALENE; NAPHTHALENE DERIVATIVE; PROTON; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; DEALKYLATION; DEMETHYLATION; HEATING; PRIORITY JOURNAL; PROTON TRANSPORT; SYNTHESIS; X RAY;

EID: 16244391463     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.02.067     Document Type: Article

References (45)

1. V. Balasubramanian Chem. Rev. 66 1966 567 641
2. I.I. Schuster, and J.D. Roberts J. Org. Chem. 45 1980 284 287
3. P.C. Bell, and J.D. Wallis Chem. Commun. 1999 257 258
4. J.D. Hoefelmeyer, M. Schulte, M. Tschinkl, and F.P. Gabbaï Coord. Chem. Rev. 235 2002 93 103
5. A.F. Pozharskii Russ. Chem. Rev. 72 2003 447 470
6. F. Hibbert, and K.J. Spiers J. Chem. Soc., Perkin Trans. 2 1989 377 380
7. A.J. Kirby, and J.M. Percy J. Chem. Soc., Perkin Trans. 2 1989 907 912
8. A. Awwal, and F. Hibbert J. Chem. Soc., Perkin Trans. 2 1977 152 156
9. E.M. Arnett, K.G. Venkatasubramaniam, R.T. McIver, E.K. Fukuda, F.G. Bordwell, and R.D. Press J. Am. Chem. Soc. 104 1982 325 326
10. A.F. Pozharskii Russ. Chem. Rev. 67 1998 1 24
11. F. Hibbert J. Chem. Soc., Perkin Trans. 2 1974 1862 1866
12. C.L. Perrin, and B.K. Ohta J. Am. Chem. Soc. 123 2001 6520 6526
13. C.L. Perrin, and B.K. Ohta J. Mol. Struct. 644 2003 1 12
14. A.F. Pozharskii, A.N. Suslov, N.M. Starshikov, L.L. Popova, N.A. Kluev, and V.A. Adanin Zh. Org. Khim. 16 1980 2216 2228 (Russ. J. Org. Chem.)
15. Kurasov, L. A. Synthesis and Properties of N-substituted 1,8-Diaminonaphthalenes; Ph.D. Thesis, Rostov State University, 1981.
16. G.C. Lloyd-Jones, J.N. Harvey, P. Hodgson, M. Murray, and R.L. Woodward Chem. Eur. J. 9 2003 4523 4535
17. E. Grech, J. Nowicka-Scheibe, Z. Olejnik, T. Lis, Z. Pawelka, Z. Malarski, and L. Sobczyk J. Chem. Soc., Perkin Trans. 2 1996 343 348
18. H.A. Staab, and T. Saupe Angew. Chem. Int. Ed. Engl. 27 1988 865 879
19. A.L. Llamas-Saiz, C. Foces-Foces, and J. Elguero J. Mol. Struct. 328 1994 297 323
20. R.W. Alder, and J.E. Anderson J. Chem. Soc., Perkin Trans. 2 1973 2086 2088
21. R.W. Alder, M.R. Bryce, N.C. Goode, N. Miller, and J. Owen J. Chem. Soc., Perkin Trans. 1 1981 2840 2847
22. A.F. Pozharskii, L.A. Kurasov, V.V. Kuz'menko, and L.L. Popova Zh. Org. Khim. 17 1981 1005 1013 (Russ. J. Org. Chem.)
23. N.V. Vistorobskii, and A.F. Pozharskii Zh. Org. Khim. 32 1996 71 75 (Russ. J. Org. Chem. 1996, 32, 61-65)
24. H.J. Reich, and M.L. Cohen J. Org. Chem. 44 1979 3148 3153
25. With strong electron-withdrawing functions in the naphthalene ring, it is possible to perform nucleophilic demethylation of free proton sponge bases. Thus, 1,8-bis(dimethylamino)-4-nitronaphthalene (7) at treatment with KOH in DMSO at 40 °C gave 1-methylamino-8-dimethylamino-4-nitronaphthalene (8) in 40% yield (a) A.F. Pozharskii, V.A. Ozeryanskii, and V.V. Kuz'menko Zh. Org. Khim. 32 1996 76 82 (Russ. J. Org. Chem. 1996, 32, 66-72)
26. In addition, for acenaphthene (b) V.A. Ozeryanskii, A.F. Pozharskii, and N.V. Vistorobskii Russ. Chem. Bull. 49 2000 1212 1217 and acenaphthylene proton sponges
27. V.A. Ozeryanskii, A.F. Pozharskii, G.R. Milgizina, and S.T. Howard J. Org. Chem. 65 2000 7707 7709 there have been described some examples of oxidative monodemethylation, for which the formation of methyleneimmonium salt followed by its hydrolysis was assumed. The oxidative mechanism has been proved to be the main pathway for the biological demethylation of N,N-dimethylanilines
28. S.B. Karki, J.P. Dinnocenzo, J.P. Jones, and K.R. Korzekwa J. Am. Chem. Soc. 117 1995 3657 3664
29. R.A. Chambers, and D.E. Pearson J. Org. Chem. 28 1963 3144 3147
30. H.A. Staab, K. Elbl-Weiser, and C. Krieger Eur. J. Org. Chem. 2000 327 333
31. A.F. Pozharskii, V.A. Ozeryanskii, and Z.A. Starikova J. Chem. Soc., Perkin Trans. 2 2002 318 322
32. A.F. Pozharskii, V.V. Kuz'menko, G.G. Alexandrov, and D.V. Dmitrienko Zh. Org. Khim. 31 1995 570 581 (Russ. J. Org. Chem.)
33. V.D. Filimonov, E.A. Krasnokutskaya, and Yu.A. Lesina Zh. Org. Khim. 39 2003 655 660 (Russ. J. Org. Chem. 2003, 39, 875-880)
34. A.F. Pozharskii, O.V. Ryabtsova, V.A. Ozeryanskii, A.V. Degtyarev, O.N. Kazheva, G.G. Alexandrov, and O.A. Dyachenko J. Org. Chem. 68 2003 10109 10122
35. L.A. Kurasov, A.F. Pozharskii, and V.V. Kuz'menko Zh. Org. Khim. 17 1981 1944 1947 (Russ. J. Org. Chem.)
36. A.F. Pozharskii, G.G. Alexandrov, and N.V. Vistorobskii Zh. Org. Khim. 27 1991 1536 1543 (Russ. J. Org. Chem.)
37. S.T. Howard J. Am. Chem. Soc. 122 2000 8238 8244
38. In order to estimate the reliability of calculated values for dipole moments of 8 and 9, Table 6 contains also the results of calculations according to the methods AM1 and PM3. They are compared with the similar data for parent proton sponge 3 and its 4,5-diformyl derivative 40, for which experimental values are also available. As it seen, for dialdehyde 40, there is a good agreement (deviation is less than 3%) between the experiment and the theory (both methods, AM1 and PM3, are almost equally acceptable). In the case of 3, the discrepancy for AM1 is inadmissibly big (∼30%), while for the PM3 method it is much less (∼10%). Therefore, the discussion of results is based on the PM3 data. It should be emphasized that, at the same time, the best correspondence in estimating the dipole moment of 3 gave ab initio calculations (see Ref. 26).
39. M. Williams, J.R. Ferraro, R.I. Thorn, K.D. Carlson, U. Geiser, H.H. Wang, A.M. Kini, and M.-H. Whangho Organic Superconductors 1992 Prentice-Hall Englewood Cliffs, NJ p 353
40. G.M. Scheldrik SHELXS 97 and SHELXL 97 1997 University of Gottingen Germany
41. V.A. Ozeryanskii, E.A. Filatova, V.I. Sorokin, and A.F. Pozharskii Russ. Chem. Bull. 50 2001 846 853
42. V.I. Sorokin, V.A. Ozeryanskii, and A.F. Pozharskii Zh. Org. Khim. 38 2002 737 746 (Russ. J. Org. Chem. 2002, 38, 699-708)
43. V.A. Ozeryanskii, V.I. Sorokin, and A.F. Pozharskii Russ. Chem. Bull. 53 2004 404 414
44. V.A. Ozeryanskii, A.F. Pozharskii, and N.V. Vistorobskii Zh. Org. Khim. 33 1997 285 290 (Russ. J. Org. Chem. 1997, 33, 251-256)
45. V.I. Sorokin, V.A. Ozeryanskii, and A.F. Pozharskii Eur. J. Org. Chem. 2003 496 498