Synthesis of Macropolycycles Comprising Diazacrown and Adamantane Moieties via Pd -Catalyzed Amination Reaction

Alexei A. Yakushev,^a,b Maksim V. Anokhin,^a Alexei D. Averin,^a,b@ Olga A. Maloshitskaya,^a Evgenii N. Savelyev,^c Gennadii M. Butov,^d Boris S. Orlinson,^c Ivan A. Novakov,^c and Irina P. Beletskaya^a,b

^aLomonosov Moscow State University, Department of Chemistry, 119991 Moscow, Russia
^bA.N. Frumkin Institute of Physical and Electrochemistry, 119991 Moscow, Russia
^cVolgograd State Technical University, 400131 Volgograd, Russia
^dVolzhsky Polytechnical Institute (Branch) of Volgograd State Technical University, 404131 Volzhsky, Russia

^@Corresponding authorE-mail: averin@org.chem.msu.ru

Macroheterocycles 2013 6(1) 40-46

DOI: 10.6060/mhc121214a

PDF

N,N’-Bis(bromobenzyl) substituted diazacrown ethers were obtained in the reactions of corresponding free diaza-crowns with two equivalents of bromobenzyl bromides in high yields. These compounds were introduced in the Pd-catalyzed amination reaction with 1,3-bis(aminomethyl) and 1,3-bis(2-aminoethyl)adamantanes to give macrobicyclic products.

References:

Click here to expand or collapse this section

1. Bouquant J., Delville A., Grandjean J., Laszlo P. J. Am. Chem. Soc. 1982, 104, 686-691.
http://dx.doi.org/10.1021/ja00367a009

2. Gruber H., Schroeder G. Liebigs Ann. Chem. 1985, 421-425.
http://dx.doi.org/10.1002/jlac.198519850219

3. Helgeson R. C., Tarnowski T. L., Cram D. J. J. Org. Chem. 1979, 44, 2538-2550.
http://dx.doi.org/10.1021/jo01328a045

4. Costero A. M., Gil S., Sanchis J., Peransi S., Sanzam V., Williams J. A. G. Tetrahedron 2004, 60, 6327-6334.
http://dx.doi.org/10.1016/j.tet.2004.05.075

5. Schmittel M., Ammon H. J. Chem. Soc., Chem. Commun. 1995, 687-688.
http://dx.doi.org/10.1039/c39950000687

6. Beer P. D., Keefe A. D., Sikanyika H., Blackburn C., McAleer J. F. J. Chem. Soc., Dalton Trans. 1990, 3289-3294.

7. Michaudet L., Richard P., Boitrel B. Tetrahedron Lett. 2000, 41, 8289-8292.
http://dx.doi.org/10.1016/S0040-4039(00)01462-3

8. Chen H., Kim Y. S., Lee J., Yoon S. J., Lim D. S., Choi H.-J., Koh K. Sensors 2007, 7, 2263-2272.
http://dx.doi.org/10.3390/s7102263

9. Bianchi A., Ciampolini M., Micheloni M., Chimichi S., Zanobini F. Gazz. Chim. Ital. 1987, 117, 499-502.

10. Bencini A., Bianchi A., Borselli A., Ciampolini M., Micheloni M., Paoli P., Valtancoli B., Dapporto P., Garcia-Espa-a E., Ramirez J.A. J. Chem. Soc., Perkin Trans. 2 1990, 209-214.
http://dx.doi.org/10.1039/p29900000209

11. Bemtegen J. M., Springer M. E., Loyola V. M., Wilkins R. G., Taylor R. W. Inorg. Chem. 1984, 23, 3348-3353.
http://dx.doi.org/10.1021/ic00189a016

12. Chapoteau E., Czech B. P., Kumar A., Pose A. J. Inclusion Phenom. 1988, 6, 41-47.
http://dx.doi.org/10.1007/BF00659367

13. Wehner W., Vögtle F. Tetrahedron Lett. 1976, 17, 2603-2606.
http://dx.doi.org/10.1016/S0040-4039(00)91745-3

14. Arnaud-Neu F., Sanchez M., Yahya R., Schwing-Weill M-J., Lehn J-M. Helv. Chim. Acta 1985, 68, 456-464.
http://dx.doi.org/10.1002/hlca.19850680219

15. Boudon C., Gisselbrecht J.P., Gross M., Kotzyba-Hibert F., Lehn J-M. J. Electroanal. Chem. 1986, 202, 191-201.
http://dx.doi.org/10.1016/0022-0728(86)90118-X

16. Graf E., Lehn J-M. Helv. Chim. Acta 1981, 64, 1040-1057.
http://dx.doi.org/10.1002/hlca.19810640410

17. Krakowiak K. E., Bradshaw J. S., Dalley N. K., Zhu Ch., Yi G., Curtis J. C., Li D., Izatt R. M. J. Org. Chem. 1992, 57, 3166-3173.
http://dx.doi.org/10.1021/jo00037a038

18. Bradshaw J. S., Krakowiak K. E., An H., Wang T., Zhu Ch., Izatt R. M. Tetrahedron Lett. 1992, 33, 4871-4874.
http://dx.doi.org/10.1016/S0040-4039(00)61220-0

19. Krakowiak K. E. J. Incl. Phen. Mol. Recogn. 1997, 29, 283-288.
http://dx.doi.org/10.1023/A:1007915815440

20. Aigami K., Inamoto Y., Takaishi N., Hattori K., Takatsuki A., Tamura G. J. Med. Chem. 1975, 18, 713-721.
http://dx.doi.org/10.1021/jm00241a015

21. Novakov I. A., Kulev I. A., Radchenko S. S., Birznieks K. A., Boreko E. I., Vladyko G. V., Korobchenko L. V. Khim.-Farm. Zh. 1987, 21, 454-458 (in Russ.).

22. Inamoto Y., Aigami K., Kadono T. Jap. Pat. 50108252, 1975 (Chem. Abstr., 1976, 84, 58783).

23. Inamoto Y., Aigami K., Hattori K., Kakuno T. Jap. Pat. 50111218, 1975 (Chem. Abstr., 1975, 83, 188517).

24. Popov Yu. V., Korchagina T. K., Chicherina G. V., Ermakova T. A. Russ. J. Org. Chem. 2002, 38, 350-354.
http://dx.doi.org/10.1023/A:1016321823035

25. Averin A. D., Ranyuk E. R., Golub S. L., Buryak A. K., Savelyev E. N., Orlinson B. S., Novakov I. A., Beletskaya I. P. Synthesis 2007, 2215-2221.
http://dx.doi.org/10.1055/s-2007-983760

26. Averin A. D., Shukhaev A. V., Buryak A. K., Denat F., Guilard R., Beletskaya I. P. Tetrahedron Lett. 2008, 49, 3950-3954.
http://dx.doi.org/10.1016/j.tetlet.2008.04.045

27. Kobelev S. M., Averin A. D., Buryak A. K., Denat F., Guilard R., Beletskaya I. P. Heterocycles 2011, 82, 1447-1476.

28. Averin A. D., Ulanovskaya M. A., Kovalev V. V., Buryak A. K., Orlinson B. S., Novakov I. A., Beletskaya I. P. Russ. J. Org. Chem. 2010, 46, 64-72.
http://dx.doi.org/10.1134/S1070428010010069

29. Averin A. D., Ulanovskaya M. A., Buryak A. K., Savelyev E. N., Orlinson B. S., Novakov I. A., Beletskaya I. P. Russ. J. Org. Chem. 2010, 46, 1790-1811.
http://dx.doi.org/10.1134/S1070428010120055

30. Averin A. D., Ranyuk E. R., Buryak A. K., Savelyev E. N., Orlinson B. S., Novakov I. A., Beletskaya I. P. Mendeleev Comm. 2009, 19, 136-138.
http://dx.doi.org/10.1016/j.mencom.2009.05.007

31. Ranyuk E. R., Averin A. D., Buryak A. K., Savelyev E. N., Orlinson B. S., Novakov I. A., Beletskaya I. P. Russ. J. Org. Chem. 2009, 45, 1555-1566.
http://dx.doi.org/10.1134/S1070428009100236

32. Averin A. D., Ulanovskaya M. A., Buryak A. K., Savelyev E. N., Orlinson B. S., Novakov I. A., Beletskaya I. P. Russ. J. Org. Chem. 2011, 47, 30-40.
http://dx.doi.org/10.1134/S1070428011010027

33. Ukai T., Kawazura H., Ishii Y., Bonnet J. J., Ibers J. A. J. Organomet. Chem. 1974, 65, 253-266.
http://dx.doi.org/10.1016/S0022-328X(00)91277-4

Attachment	Size
mhc2013_t06n1_40-46.pdf	681.31 KB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search