A Study of the Reaction between Methylpyropheophorbide a and Hydrazine Hydrate

Ivan S. Lonin,^a@ Evgeny S. Belyaev,^a Aslan Yu. Tsivadze,^a Gelii V. Ponomarev,^b Natalya N. Lonina,^c Andrew N. Fitch,^d and Vladimir V. Chernyshev^a,e

Dedicated to Academician of Russian Academy of Sciences Aslan Yu. Tsivadze on the occasion of his Birthday

^aA.N. Frumkin Institute of Physical Chemistry and Electrochemistry of Russian Academy of Sciences, 119071 Moscow, Russia

^bResearch Institute of Biomedical Chemistry, 119121 Moscow, Russia

^cMoscow Technological University, Institute of Fine Chemical Technologies, 119571 Moscow, Russia

^dEuropean Synchrotron Radiation Facility, B. P. 220, 38043 Grenoble Cedex, France

^eChemical Department, Moscow State University, 119991 Moscow, Russia

^@Corresponding author E-mail: loninis@gmail.com

DOI: 10.6060/mhc170832l
Macroheterocycles 2017 10(4-5) 474-479

The reaction between pyropheophorbide a methyl ester (1) and hydrazine hydrate has been studied. It was shown that the reagents ratio governs the particular reaction product formation. Treatment of 1 by excess of hydrazine hydrate (more than 3 eq.) yielded methylmesopyropheophorbide a hydrazone (2) as a major product. On the other hand, only methylmesopyropheophorbide a azine (4) was formed when the equimolar amounts of the reagents were applied. In order to prevent the C3-vinyl group reduction in 1 by hydrazine hydrate, the reaction was carried out in the presence of trifluoroacetic acid (TFA). It was shown, that the selectivity of the reaction is regulated by the hydrazine hydrate/TFA ratio. Thus, the optimal conditions for the selective synthesis of both methylpyropheophorbide a hydrazone (3) and azine (5) have been found. The formation of the dimeric structure of azines was determined by the X-ray powder diffraction.

References:

Click here to expand or collapse this section

1. Wang X.-F., Kitao O. Molecules 2012, 17, 4484–4497.
https://doi.org/10.3390/molecules17044484

2. Yoon I., Li J.Z., Shim Y.K. Clinical Endoscopy 2013, 46, 7–23.
https://doi.org/10.5946/ce.2013.46.1.7

3. Borisov S.M., Papkovsky D.B., Ponomarev G.V., DeToma A.S., Saf R., Klimant I. J. Photochem. Photobiol. A: Chem. 2009, 206, 87–92.
https://doi.org/10.1016/j.jphotochem.2009.05.018

4. Zhuang T., Sasaki S., Ikeuchi T., Kido J., Wang X.-F. RSC Adv. 2015, 5, 45755–45759.
https://doi.org/10.1039/C5RA07099F

5. Tamiaki H., Tanaka T., Wang X.-F. J. Photochem. Photobiol. A: Chem. 2015, 313, 19–26.
https://doi.org/10.1016/j.jphotochem.2015.05.003

6. Wang X.-F., Tamiaki H., Kitao O., Ikeuchi T., Sasaki S. J. Power Sources 2013, 242, 860–864.
https://doi.org/10.1016/j.jpowsour.2013.05.191

7. Hug H., Bader M., Mair P., Glatzel T. Applied Energy 2014, 115, 216–225.
https://doi.org/10.1016/j.apenergy.2013.10.055

8. Li Y., Li H., Song P., Sun C. Journal of Nanomaterials 2015, 1–6.

9. Yamamoto Y., Tamiaki H. Dyes Pigments 2015, 118, 159–165.
https://doi.org/10.1016/j.dyepig.2015.03.006

10. Okamoto Y., Tamiaki H. J. Photochem. Photobiol. A: Chem. 2011, 219, 250–254.
https://doi.org/10.1016/j.jphotochem.2011.02.027

11. Liu M., Chen C.-Y., Mandal A.K., Chandrashaker V., Evans-Storms R.B., Pitner J.B., Bocian D.F., Holten D., Lindsey J.S. New J. Chem. 2016, 40, 7721–7740.
https://doi.org/10.1039/C6NJ01154C

12. Sasaki S., Mizutani K., Kunieda M., Tamiaki H. Tetrahedron 2011, 67, 6065–6072.
https://doi.org/10.1016/j.tet.2011.06.020

13. Kinoshita Y., Kunieda M., Mikata Y., Tamiaki H. Tetrahedron Lett. 2013, 54, 1243–1246.
https://doi.org/10.1016/j.tetlet.2012.12.100

14. Sasaki S., Mizutani K., Kunieda M., Azuma K., Tamiaki H. Chem. Lett. 2013, 42, 1212–1213.
https://doi.org/10.1246/cl.130564

15. Nikkonen T., Oliva M.M., Taubert S., Melchionna M., Kahnt A., Helaja J. Chem. Eur. J. 2015, 21, 12755–12768.
https://doi.org/10.1002/chem.201501856

16. Tamiaki H., Kuno M., Kunieda M. Tetrahedron Lett. 2014, 55, 2825–2828.
https://doi.org/10.1016/j.tetlet.2014.03.071

17. Tamiaki H., Koizumi S., Tsuji K., Kinoshita Y., Miyatake T. Tetrahedron Lett. 2014, 55, 1093–1096.
https://doi.org/10.1016/j.tetlet.2013.12.099

18. Wang J.-J., Han G.-F., Shim Y.K. Journal of Photoscience 2001, 8(1), 23–25.

19. Lonin I.S., Kuzovlev A.S., Belyaev E.S., Ponomarev G.V., Oskar I.K., Tsivadze A.Yu. J. Porphyrins Phthalocyanines 2014, 18, 123–128.
https://doi.org/10.1142/S108842461350123X

20. Kenner G.W., McCombie S.W., Smith K.M. J. Chem. Soc. Perkin I, 1973, 2517–2523.
https://doi.org/10.1039/p19730002517

21. Gottlieb H.E., Kotlyar V., Nudelman A. J. Org. Chem. 1997, 62, 7512–7515.
https://doi.org/10.1021/jo971176v

22. Werner P.-E., Eriksson L., Westdahl M. J. Appl. Crystallogr. 1985, 18, 367−370.
https://doi.org/10.1107/S0021889885010512

23. Visser J.W. J. Appl. Crystallogr. 1969, 2, 89−95.
https://doi.org/10.1107/S0021889869006649

24. Zlokazov V.B. J. Appl. Crystallogr. 1992, 25, 69−72.
https://doi.org/10.1107/S0021889891009366

25. Zlokazov V.B. Comput. Phys. Commun. 1995, 85, 415−422.
https://doi.org/10.1016/0010-4655(94)00151-Q

26. Pawley G.S. J. Appl. Crystallogr. 1981, 14, 357−361.
https://doi.org/10.1107/S0021889881009618

27. Zhukov S.G., Chernyshev V.V., Babaev E.V., Sonneveld E.J., Schenk H. Z. Kristallogr. 2001, 216, 5−9.
https://doi.org/10.1524/zkri.216.1.5.18998

28. Zlokazov V.B., Chernyshev V.V. J. Appl. Crystallogr. 1992, 25, 447−451.
https://doi.org/10.1107/S0021889891013122

29. Laikov D.N. Chem. Phys. Lett. 1997, 281, 151–154.
https://doi.org/10.1016/S0009-2614(97)01206-2

30. Laikov D.N. 2004. PRIRODA. Moscow State University.

31. Laikov D.N. Chem. Phys. Lett. 2005, 416, 116–120.
https://doi.org/10.1016/j.cplett.2005.09.046

32. Laikov D.N., Ustynyuk Y.A. Russ. Chem. Bull. 2005, 54, 820–826.
https://doi.org/10.1007/s11172-005-0329-x

33. Perdew J.P.S., Burke S., Ernzerhof M. Phys. Rev. Lett. 1996, 77, 3865–3868.
https://doi.org/10.1103/PhysRevLett.77.3865

34. Barluenga J., Vald C. Angew. Chem. Int. Ed. 2011, 50, 7486–7500.
https://doi.org/10.1002/anie.201007961

35. Korotchenko V.N., Shastin A.V., Nenajdenko V.G., Balenkova E.S. J. Chem. Soc., Perkin Trans. 2002, 1, 883–887.
https://doi.org/10.1039/b201131j

36. Korotchenko V.N., Nenajdenko V.G., Shastin A.V., Balenkova E.S. Org. Biomol. Chem. 2003, 1, 1906–1908.
https://doi.org/10.1039/b303221c

37. Li J.Z., Li L., Kim J.H., Cui B.C., Wang J.J., Shim Y.K. J. Porphyrins Phthalocyanines 2011, 15, 264–270.
https://doi.org/10.1142/S1088424611003239

38. Mironov A.F., Grin M.A., Nochovny S.A., Toukach P.V. Mendeleev Commun. 2003, 13(4), 156–157.
https://doi.org/10.1070/MC2003v013n04ABEH001735

39. Kolb V.M., Kuffel A.C., Spiwek H.O., Janota T.E. J. Org. Chem. 1989, 54, 2771–2775.
https://doi.org/10.1021/jo00272a064

40. Furrow M.E., Myers A.G. J. Am. Chem. Soc. 2004, 126, 5436–5445.
https://doi.org/10.1021/ja049694s

41. Miller C.E. J. Chem. Educ. 1965, 42, 254–259.
https://doi.org/10.1021/ed042p254

42. Spek A.L. Acta Crystallogr. D 2009, D65, 148–155.
https://doi.org/10.1107/S090744490804362X

43. Groom C.R., Allen F.H. Angew. Chem. Int. Ed. 2014, 53, 662–671.
https://doi.org/10.1002/anie.201306438

44. Macrae C.F., Bruno I.J., Chisholm J.A., Edgington P.R., McCabe P., Pidcock E., Rodriguez-Monge L., Taylor R., van de Streek J., Wood P.A. J. Appl. Crystallogr. 2008, 41, 466–470.
https://doi.org/10.1107/S0021889807067908

Attachment	Size
mhc170832l.pdf	1.07 MB

Журнал "Макрогетероциклы"

Navigation

Languages

News

Search

A Study of the Reaction between Methylpyropheophorbide a and Hydrazine Hydrate

References: