Synthesis of 4-Nitro- and 4-Aminophenylazacrown Ethers

Aleksandr S. Oshchepkov,^a,c Maksim S. Oshchepkov,^b,c Alexander V. Anisimov,^a and Olga A. Fedorova^a,b,c@

^аChemistry Department, M.V. Lomonosov Moscow State University, 119992 Moscow, Russia

^bD.I. Mendeleev University of Chemical Technology of Russia,125047 Moscow, Russia

^cA.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, 119991 Moscow, Russia

^@Corresponding E-mail: fedorova@ineos.ac.ru

The study is dedicated to finding optimal reaction conditions for the introduction of 4-nitro- and 4-aminophenyl substituents into the structure of azacrown ethers with a varied ratio of oxygen to nitrogen heteroatoms. The synthetic procedure is proposed for the synthesis of 4-nitroaryl derivatives of crown ethers. This method is remarkably simple, has easy work-up and affords the formation solely of the monoarylation product.

References:

Click here to expand or collapse this section

1. Adachi G.-Y., Hirashima Y. Macrocyclic complexes of lanthanide ions. In: Cation Binding by Macrocycles. Complexation of Cationic Species by Crown Ethers (Inoue Y., Gokel G.W., Eds.), New York: Marcel Dekker, 1990, 701–741.

2. Izatt R. M., Pawlak K., Bradshaw J. S., Bruening R. L. Chem. Rev. 1991, 91, 1721–2085.

http://dx.doi.org/10.1021/cr00008a003

3. Yordanov A. T., Roundhill D. M. Coord. Chem. Rev. 1998, 170, 93–124.

http://dx.doi.org/10.1016/S0010-8545(97)00074-X

4. Gloe K., Graubaum H., Wust M., Rambusch T., Seichter W. Coord. Chem. Rev. 2001, 222, 103–126.

http://dx.doi.org/10.1016/S0010-8545(01)00397-6

5. Buhlmann P., Pretsch E., Bakker E. Chem. Rev. 1998, 98, 1593–1687.

http://dx.doi.org/10.1021/cr970113+

6. Feiters M.C. In: Comprehensive Supramolecular Chemistry, Vol. 10 (Reinhoudt D.N., Ed.), Oxford: Pergamon Press, 1996, 267–360.

7. 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, 1515–1566.

http://dx.doi.org/10.1021/cr960386p

8. Fedorova O.A., Fedorov Yu.V., Panchenko P.A., Sergeeva A.N., Oshchepkov M.S., Oshchepkov A.S. RU Patent No 2515195, Bull. No 13, p. 2 (in Russ.).

9. Gokel G.W., Korzeniowski S.H. Macrocyclic Polyether Synthesis. Berlin: Springer-Verlag, 1982, 410 p.

http://dx.doi.org/10.1002/ange.19830950733

10. Krakowiak K.E., Bradshaw J.S., Zamecka-Krakowiak D.J. Chem. Rev. 1989, 89, 929–972.

http://dx.doi.org/10.1021/cr00094a008

11. Bradshaw J.S., Krakowiak K.E., Izatt R.M. Benzoaza-Crown Macrocycles. In: Chemistry of Heterocyclic Compounds: Aza-Crown Macrocycles, Vol. 51, Hoboken: John Wiley & Sons, Inc., 1993.

http://dx.doi.org/10.1002/9780470187388.ch8

12. Elwahy A.H.M. J. Heterocycl. Chem. 2003, 40, 1–23.

http://dx.doi.org/10.1002/jhet.5570400101

13. Dix J.P., Vogtle F. Angew. Chem. 1978, 90, 893–895.

http://dx.doi.org/10.1002/ange.19780901109

14. Dix J. P., Vogtle F. Chem. Ber. 1980, 113, 457–470.

http://dx.doi.org/10.1002/cber.19801130206

15. Oshchepkov M.S., Perevalov V.P., Kuzmina L.G., Anisimov A.V., Fedorova O.A. Russ. Chem. Bull., Int. Ed. 2011, 3, 478–485.

http://dx.doi.org/10.1007/s11172-011-0075-1

16. Fedorova O., Fedorov Y., Oshchepkov M. Electroanalysis 2012, 24, 1739–1744.

http://dx.doi.org/10.1002/elan.201200134

17. Fedorova O., Fedorov Y., Oshchepkov M., Dobrovolskaya M. J. Phys. Org. Chem. 2012, 25, 835–839.

http://dx.doi.org/10.1002/poc.2926

18. Fedorov Yu.V., Fedorova O.A., Gromov S.P., Bobrovskii M.B., Andryukhina E.N., Alfimov M.V. Russ. Chem. Bull., Int. Ed. 2002, 51, 789–795.

http://dx.doi.org/10.1023/A:1016072414801

19. Subat M., Konig B. Synthesis 2001, 1818–1825.

http://dx.doi.org/10.1055/s-2001-17531

20. Witulski B. Synlett 1999, 1223–1226.

http://dx.doi.org/10.1055/s-1999-2799

21. Beletskaya I.P., Averin A.D., Bessmertnykh A.G., Denat F., Guilard R. Tetr. Lett. 2002, 43, 1193–1196.

http://dx.doi.org/10.1016/S0040-4039(01)02356-5

22. Leska B., Schroder G., Gierczyk B. ACH–Models in Chem. 1996, 133, 461–462.

23. Gierczyk B., Leska B., Nowak-Wydra B., Schroder G., Wojciechowski G., Bartl F., Brzezinski B. J. Mol. Struct. 2000, 524, 217–225.

http://dx.doi.org/10.1016/S0022-2860(00)00379-3

24. Collins G.E., Choi L.-S., Callahan J.H. J. Am. Chem. Soc. 1998, 120, 1474–1478.

http://dx.doi.org/10.1021/ja972169r

25. Koike T., Gotoh T., Aoki S., Kimura E., Shiro M. Inorg. Chim. Ada 1998, 270, 424–432.

http://dx.doi.org/10.1016/S0020-1693(97)05998-7

26. Boiocchi M., Fabbrizzi L., Licchelli M., Sacchi D., Vázquez M., Zampa C. Chem. Commun. 2003, 1812–1813.

http://dx.doi.org/10.1039/B305456J

27. Jana A., Kumar De A., Nag A., Goswami D., Bharadwaj P.K. Organometall. Chem. 2008, 693, 1186–1194.

http://dx.doi.org/10.1016/j.jorganchem.2008.01.019

28. Saglik B.N., Özkay Y., Özkay Ü.D., Gener H.K. Journal of Chemistry 2014, 2014, Article ID 387309.

29. Arundhathi R., Kumar D.Ch., Sreedhar B. Eur. J. Org. Chem. 2010, 19, 3621–3630.

http://dx.doi.org/10.1002/ejoc.201000149

30. Gromov S.P., Ushakov E.N., Fedorova O.A., Soldatenkova V.A., Alfimov M.V. Izv. AN, Ser. Khim. 1997, 6, 1192–1197. (in Russ.)

31. Terreno E., Boniforte P., Botta M., Fedeli F., Milone L., Mortillaro A., Aime S. Eur. J. Inorg. Chem. 2003, 3530–3533.

http://dx.doi.org/10.1002/ejic.200300356

32. Deveci P., Taner B., Üstündag Z., Özcan E., Solak A.O., Kılıç Z. J. Mol. Str. 2010, 982, 162–168.

http://dx.doi.org/10.1016/j.molstruc.2010.08.024

Attachment	Size
mhc150247f.pdf	399.78 KB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

References: