A novel ring transformation of nitrobenzocrown ethers as a route to nitrobenzoazacrown compounds

Synthesis

Volumn , Issue 4, 2003, Pages 593-597

  Gromov, Sergey P ^a   Dmitrieva, Svetlana N ^a   Churakova, Marina V ^a  

^a PHOTOCHEMISTRY CENTER   (Russian Federation)

Author keywords

Crown compounds; Nitrobenzoazacrown compounds; Podands; Ring closure; Ring opening

Indexed keywords

BENZENE; NITROGEN; SYNTHESIS (CHEMICAL);

RING TRANSFORMATION;

ETHERS;

BENZENE DERIVATIVE; CROWN ETHER DERIVATIVE; NITROBENZOAZACROWN DERIVATIVE; NITROBENZOCROWN ETHER DERIVATIVE; NITROGEN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; RING OPENING; SYNTHESIS;

EID: 0037241145     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37662     Document Type: Article

References (32)

1. (a) Cation Binding by Macrocycles; Inoue, Y.; Gokel, G. W., Eds.; Marcel Dekker: New York, 1990.
2. (b) Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L. Chem. Rev. 1991, 91, 1721.
3. (a) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
4. (b) Alfimov, M. V.; Gromov, S. P. In Applied Fluorescence in Chemistry, Biology, and Medicine; Rettig, W.; Strehmel, B.; Schrader, S.; Seifert, H., Eds.; Springer Verlag: Berlin, 1999, 161.
5. (c) Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3.
6. (d) Shinkai, S. In Comprehensive Supramolecular Chemistry, Vol. 1; Gokel, G. W., Ed.; Pergamon: Oxford, 1996, 671.
7. (e) Gromov, S. P.; Alfimov, M. V. Russ. Chem. Bull.; 1997, 46: 611. Izv. Akad. Nauk, Ser. Khim. 1997, 641.
8. (e) Gromov, S. P.; Alfimov, M. V. Russ. Chem. Bull.; 1997, 46: 611. Izv. Akad. Nauk, Ser. Khim. 1997, 641.
9. (f) Mishra, A.; Behera, R. K.; Behera, P. K.; Mishra, B. K.; Behera, G. B. Chem. Rev. 2000, 100, 1973.
10. (a) Yordanov, A. T.; Roundhill, D. M. Coord. Chem. Rev. 1998, 170, 93.
11. (b) Gloe, K.; Graubaum, H.; Wüst, M.; Rambusch, T.; Seichter, W. Coord. Chem. Rev. 2001, 222, 103.
12. Bühlmann, P.; Pretsch, E.; Bakker, E. Chem. Rev. 1998, 98, 1593.
13. Feiters, M. C. In Comprehensive Supramolecular Chemistry, Vol. 10; Reinhoudt, D. N., Ed.; Pergamon: Oxford, 1996, 267.
14. (a) Bradshaw, J. S.; Krakowiak, K. E.; Izatt, R. M. AzaCrown Macrocycles; Wiley: New York, 1993.
15. (b) Krakowiak, K. E.; Bradshaw, J. S.; Zamecka-Krakowiak, D. J. Chem. Rev. 1989, 89, 929.
16. (a) Lockhart, J. C.; Robson, A. C.; Thompson, M. E.; Furtado, S. D.; Kaura, C. K.; Allan, A. R. J. Chem. Soc., Perkin Trans. 1 1977, 202.
17. (b) Pedersen, C. J.; Bromels, M. H. US Patent 3847949, 1974; Chem. Abstr. 1975, 82, 73049.
18. (b) Pedersen, C. J.; Bromels, M. H. US Patent 3847949, 1974; Chem. Abstr. 1975, 82, 73049.
19. Högberg, S. A. G. Cram, D. J. J. Org. Chem. 1975, 40, 151.
20. (d) Lockhart, J. C.; Thompson, M. E. J. Chem. Soc., Perkin Trans. 1 1977, 202.
21. (a) Kost, A. N.; Gromov, S. P.; Sagitullin, R. S. Tetrahedron 1981, 37, 3423.
22. (b) Gromov, S. P.; Kost, A. N. Heterocycles 1994, 38, 1127.
23. (c) Gromov, S. P. Heterocycles 2000, 53, 1607.
24. (a) Ivanov, E. I.; Terent'ev, P. B.; Polischuk, A. A.; Zakharov, K. S.; Subbotin, B. S. Khim. Geterotsikl, Soedin. 1985, 1573; Chem. Abstr. 1987, 106, 4591y.
25. (a) Ivanov, E. I.; Terent'ev, P. B.; Polischuk, A. A.; Zakharov, K. S.; Subbotin, B. S. Khim. Geterotsikl, Soedin. 1985, 1573; Chem. Abstr. 1987, 106, 4591y.
26. (b) Töke, L.; Bitter, I.; Agai, B.; Hell, Z.; Lindner, E.; Toth, K.; Horvath, M. A.; Szöllosy, A.; Harfouch, S.; Pungor, E. Liebigs Ann. Chem. 1988, 761.
27. (a) Gromov, S. P.; Vedernikov, A. L.; Dmitrieva, S. N. Russ. Chem. Bull.; 1999, 48: 1190. Izv. Akad. Nauk, Ser. Khim. 1999, 1204.
28. (a) Gromov, S. P.; Vedernikov, A. L.; Dmitrieva, S. N. Russ. Chem. Bull.; 1999, 48: 1190. Izv. Akad. Nauk, Ser. Khim. 1999, 1204.
29. (b) Gromov, S. P.; Vedernikov, A. I.; Dmitrieva, S. N. RF Patent 2161153, 2000; Chem. Abstr. 2002, 136, 401792.
30. (b) Gromov, S. P.; Vedernikov, A. I.; Dmitrieva, S. N. RF Patent 2161153, 2000; Chem. Abstr. 2002, 136, 401792.
31. (a) Pacey, G. E.; Wu, Y. P.; Bubnis, B. P. Synth. Commun. 1981, 11, 323.
32. (b) Ungaro, R.; El Haj, B.; Smid, J. J. Am. Chem. Soc. 1976, 98, 5198.