N-alkylation of 2,3-dihydroimidazo[2,1-b]quinazolin-1(10)H-5-one. on the cryptoanionic mechanism of N-substitution

Russian Chemical Bulletin

Volumn 55, Issue 5, 2006, Pages 907-919

  Morkovnik, A S ^a   Divaeva, L N ^a   Kuz'Menko, T A ^a  

^a SOUTHERN FEDERAL UNIVERSITY   (Russian Federation)

Author keywords

2,3 dihydroimidazo 2,1 b quinazolin 1(10)H 5 one; Cryptoanionic reaction mechanism; Density functional method; H bonded dimers; Mechanism of alkyltransferase action; N alkylation; Prototropic tautomerism; Quantum chemical calculations; Transition states

Indexed keywords

EID: 33748922799     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-006-0351-7     Document Type: Article

References (31)

1. G. H. Hardtmann, G. Koletar, and O. R. Pfister, J. Med. Chem., 1975, 18, 447.
2. G. H. Hardtmann, US Pat. 3833652; http://www.chemweb.com/databases/ patents/.
3. G. H. Hardtmann, US Pat. 3912731; http://www.chemweb.com/databases/ patents/.
4. G. H. Hardtmann, US Pat. 3919210; http://www.chemweb.com/databases/ patents/.
5. G. H. Hardtmann, US Pat. 3969506; http://www.chemweb.com/databases/ patents/.
6. N. P. Peet and Sh. Sunder, US Pat. 4871732; http://www.chemweb.com/ databases/patents/.
7. G. H. Hardtmann, US Pat. 3598823; http://www.chemweb.com/databases/ patents/
8. T. Jen, B. Dienel, H. Bowman, J. Petta, A. Helt, and B. Loev, J. Med. Chem., 1972, 15, 727.
9. E. Takeuchi and T. Sato, Jpn Pat. 61115083; http://v3.espacenet.com.
10. M. O. Sinnokrot and C. D. Sherrill, J. Am. Chem. Soc., 2004, 126, 7690.
11. H.-S. Lee, D.-Y. Cheong, S.-D. Yoh, W.-S. Kim, Y.-W. Kwak, Y.-T. Park, and J.-K. Lee, Bull. Korean Chem. Soc., 2001, 22, 633.
12. G. S. Hammond, J. Am. Chem. Soc., 1955, 77, 334.
13. T. N. Truong, T.-T. T. Truong, and E. V. Stefanovich, J. Chem. Phys., 1997, 107, 1881.
14. J. Gao and X. Xia, J. Am. Chem. Soc., 1993, 115, 9667.
15. S. P. Webb and M. S. Gordon, J. Phys. Chem. A, 1999, 103, 1265.
16. M. Sola, A. Lledos, M. Duran, J. Bertran, and J. M. Abboud, J. Am. Chem. Soc., 1991, 113, 2873.
17. J. March, Advaced Organic Chemistry, Reactions, Mechanisms and Structure, Wiley-Interscience Publication, New York. 1985.
18. D. K. Bohme and A. B. Raksit. J. Am. Chem. Soc., 1984, 106, 3447.
19. E. Humeres, R. J. Nunes, V. G. Machado, M. D. G. Gasques, and C. Machado, J. Org. Chem., 2001, 66, 1163.
20. K. C. Westaway, Y. Gao, and Y. Fang, J. Org. Chem., 2003, 68, 3084.
21. M. L. Glowka, A. Olczak, and L. Korzycka, J. Chem. Crystallogr., 1994, 24, 725.
22. W. J. Le Noble, Synthesis, 1970, 1.
23. K. Hori, J.-L. M. Abboud, C. Lim, M. Fujio, and Y. Tsuno, J. Org. Chem., 1998, 63, 4228.
24. S. D. Yoh, M.-K. Lee, K.-J. Son, D.-Y. Cheong, I. Han, and K.-T. Shim, Bull. Korean Chem. Soc., 1999, 20, 466.
25. Y. Takata, Y. Huang, J. Komoto, T. Yamada, K. Konishi, H. Ogawa, T. Gomi, M. Fujioka, and F. Takusagawa, Biochemistry, 2003, 42, 8394.
26. J. Komoto, T. Yamada, Y. Takata, K. Konishi, H. Ogawa, T. Gomi, M. Fujioka, and F. Takusagawa, Biochemistry, 2004, 43, 14385.
27. P. Velichkova and F. Himo, J. Phys. Chem. B, 2005, 109, 8216.
28. P. Velichkova and F. Himo, J. Phys. Chem. B. 2005, 109; ASAP Web Release, Date: 07-Dec-2005.
29. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su, T. L. Windus, M. Dupuis, and J. A. Montgomery, J. Comput. Chem., 1993, 14, 1347.
30. M. N. Glukhovstev, A. Pross, M. P. McGrath, and L. Radom, J. Chem. Phys., 1995, 103, 1878.
31. K. K. Irikura, R. D. Johnson III. and R. N. Kacker, J. Phys. Chem. A, 2005, 109, 8430.