Phenyl Substituted Porphyrins. Part 5. Acylation of Aminophenylporphyrins

Mariya A. Salnikova, Tatiana V. Lubimova, Aleksey V. Glazunov, Sergei A. Syrbu,^@ and Alexander S. Semeikin

Dedicated to Corresponding member of Russian Academy of Sciences Prof. Oscar I. Koifman on the occasion of his 70th Birthday

Ivanovo State University of Chemistry and Technology, 153000 Ivanovo, Russia

Institute of Solution Chemistry, Russian Academy of Science, 153045 Ivanovo, Russia

^@Corresponding author E-mail: syrbu@isuct.ru

DOI: 10.6060/mhc140510s
Macroheterocycles 2014 7(3) 249-255

Conditions of acylation of aminotetraphenylporphyrins in the presence of carbodiimides were studied. Optimal reaction conditions were determined and a number of tetraphenylporphyrin amides of various structure were synthesized.

References:

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1. Salnikova M.A., Lubimova T.V., Glazynov A.V., Syrbu S.A., Semeikin A.S., Koifman O.I. Macroheterocycles 2013, 6, 53-58.
http://dx.doi.org/10.6060/mhc130118s

2. Ruzie C., Gueyrard D., Boitrel B. Tetrahedron Lett. 2004, 45, 1713-1716.
http://dx.doi.org/10.1016/j.tetlet.2003.12.100

3. Lochner M., Mu L., Woggon W.-D. Adv. Synth. Catal. 2003, 345, 743-765.
http://dx.doi.org/10.1002/adsc.200303011

4. Stangel C., Ladomenou K., Charalambidis G., Panda M. K., Lazarides T. and Coutsolelos A. G. Eur. J. Inorg. Chem. 2013, 1275-1286.
http://dx.doi.org/10.1002/ejic.201201248

5. Myles A.J., Branda N.R. Tetrahedron Lett. 2000, 41, 3785- 3788.
http://dx.doi.org/10.1016/S0040-4039(00)00503-7

6. Shi B., Scobie M., Boyle R.W. Tetrahedron Lett. 2003, 44, 5083-5086.
http://dx.doi.org/10.1016/S0040-4039(03)01142-0

7. Bogadskiy A.V., Zhilina Z.I., Krasnoschyokaya S.P., Zakharova R.M. Zh. Org. Khim. 1982, 18(11), 2304-2309 (in Russ.).

8. Filho J.C.S., Ferreira A.G., Gotardo M.C.A.F., Assis M. das D. J. Porphyrins Phthalocyanines 2005, 9, 637-645.
http://dx.doi.org/10.1142/S1088424605000745

9. El-Kasmi A., Lexa D., Maillard P., Momenteau M., Saveant J.-M. J. Am. Chem. Soc. 1991, 113, 1586-1595.
http://dx.doi.org/10.1021/ja00005a022

10. Halime Z., Michaudet L., Lachkar M., Brossier P., Boitrel B. Bioconjugate Chem. 2004, 15, 1193-1200.
http://dx.doi.org/10.1021/bc049844o

11. Ballester D., Costa A., Deya P.M., Frontera A. et al. J. Org. Chem. 2005, 70, 6616-6622.
http://dx.doi.org/10.1021/jo0505369

12. Gunter M.J., Mander L.N. J. Org. Chem. 1981, 46, 4792- 4795.
http://dx.doi.org/10.1021/jo00336a037

13. Wang C.-w., Ren Y.-j., Cao Z.-f., Chen Q.-b. Chem. Res. Chinese Universities. 2010, 26, 761-767.

14. Laakso J., Rosser G.A., Szijjártó C., Beeby A., Borbas K.E. Inorg. Chem. 2012, 51, 10366-10374.

15. Buckingham D.A., Gunter M.J., Mander L.N. J. Am. Chem. Soc. 1978, 100, 2899-2901.
http://dx.doi.org/10.1021/ja00477a059

16. Zhang H.-L., Shi W.-M., Wu J. Heterocycles 2005, 65, 3001- 3006.
http://dx.doi.org/10.3987/COM-05-10555

17. Shi D.-F., Wheelhouse R.T., Sun D., Hurley L.H. J. Med. Chem. 2001, 44, 4509-4523.
http://dx.doi.org/10.1021/jm010246u

18. Semenishyn N.N., Rusakova N.V., Mazepa A.V., Korovin Y.V. Macroheterocycles 2009, 2, 57-59.

19. Ormond A.B., Freeman H.S. Dyes Pigm. 2013, 96, 440-448.
http://dx.doi.org/10.1016/j.dyepig.2012.09.011

20. Koga H., Hamada T., Sakaki S. Dalton Trans. 2003, 1153- 1160.
http://dx.doi.org/10.1039/b211125j

21. Weimin S., Gen Z., Guifi D., Yunxiao Z. et al. Bioorg. Med. Chem. 2008, 16, 5665-5671.
http://dx.doi.org/10.1016/j.bmc.2008.03.063

22. Imahori H., Kashiwagi Y., Endo Y., Hanada T., Nishimura Y., Yamazaki I., Araki Y., Ito O., Fukuzumi S. Langmuir 2004, 20, 73-81.
http://dx.doi.org/10.1021/la035435p

23. Hasobe T., Rabbani M.G., Sandanayaka A.S.D. et al. Chem. Commun. 2010, 46, 889-891.
http://dx.doi.org/10.1039/B915983E

24. Rojkiewicz M., Kus P., Kozub P., Kempa M. Dyes Pigm. 2013, 99, 627-635.
http://dx.doi.org/10.1016/j.dyepig.2013.06.029

25. Banfi S., Caruso E., Gariboldi M., Alemani S., Nasini G., Bombardelli E. Synth. Commun. 2008, 38, 1096-1109.
http://dx.doi.org/10.1080/00397910701863152

26. Sol V., Blais J.C., Bolbach G., Carre V. et al. Tetrahedron Lett. 1997, 38, 36, 6391-6394.
http://dx.doi.org/10.1016/S0040-4039(97)01489-5

27. Semeikin A.S., Koifman O.I., Berezin B.D. Khim. Geterotsikl. Soed. 1982, 10, 1354-1355 (in Russ.).

28. Pechnikova N.L., Lyubimtsev A.V., Syrbu S.A., Ageeva T.A., Semeikin A.S. Russ. J. Gen. Chem. 2013, 83, 99-105.
http://dx.doi.org/10.1134/S1070363213010179

29. Luguya R., Jaquinod L., Fronczek F.R., Vicente M.G.H., Smith K.M. Tetrahedron 2004, 60, 2757-2763.
http://dx.doi.org/10.1016/j.tet.2004.01.080

30. Kolodina E.A., Syrbu S.A., Semeikin A.S., Koifman O.I. Russ. J. Org. Chem. 2010, 46, 138-143.
http://dx.doi.org/10.1134/S107042801001015X

31. Mikhalitsyna E.A., Tyurin V.S., Nefedov S.E., Syrbu S.A., Semeikin A.S., Koifman O.I., Beletskaya I.P. Eur. J. Inorg. Chem. 2012, 36, 5979-5990.
http://dx.doi.org/10.1002/ejic.201200868

32. Kolodina E.A., Lubimova T.V., Syrbu S.A., Semeikin A.S. Macroheterocycles 2009, 2, 33-41.

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