A Sterically Driven Approach to the Efficient Synthesis of Low-Symmetry 1,4-Diazepinoporphyrazines

Pavel A. Tarakanov,^a@ Anton O. Simakov,^b Ekaterina N. Tarakanova,^a Alexander V. Chernyak,^c,d Vladislav Klykov,^e Pavel A. Stuzhin,^e and Victor E. Pushkarev^a

^aInstitute of Physiologically Active Compounds, Russian Academy of Sciences, 142432 Chernogolovka, Russian Federation

^bHylleraas Centre for Quantum Molecular Sciences, Department of Chemistry, University of Oslo, N-0315 Oslo, Norway

^cInstitute of Problems of Chemical Physics, Russian Academy of Sciences, 142432 Chernogolovka, Russian Federation

^dScience Center in Chernogolovka RAS, 142432 Chernogolovka, Russian Federation

^eResearch Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology, 153000 Ivanovo, Russia

^@Corresponding author E-mail: tarakanov_pa@ipac.ac.ru

DOI: 10.6060/mhc180484t
Macroheterocycles 2018 11(3) 312-315

We have investigated the general applicability of the synthetic procedure in which a carbonyl compound (in our case, 2,4-pentandione and 3-n-propyl-2,4-pentanedione) is added to a preformed TiCl₄–diaminomaleonitrile complex for the preparation of 1,4-diazepine-2,3-dicarbonitriles. It has been shown that triethylamine commonly used as an auxiliary reagent (base) inhibits the formation of the TiCl₄–diaminomaleonitrile complex and less basic pyridine was proved to be more suitable. The introduction of the n-propyl group into the C6 position of 5,7-bis(2'-arylethenyl)-6H-1,4-diazepine-2,3-dicarbonitrile has led to an unprecedented increase in the yield of the low-symmetry A₃B-type tribenzodiazepinoporphyrazine from 5 to 40 % under Linstead cross-macrocyclization conditions. The quantum-chemical calculations at the PW6B95-D3/def2-TZVP//BP86-D3/def2-TZVP level of theory demonstrated that steric effects of substituents in 6-alkyl substituted 5,7-bis(2′-arylethenyl)-6H-1,4-diazepine-2,3-dicarbonitriles can play a key role in formation of dimeric intermediates during Linstead macrocyclization, providing high selectivity towards low symmetry porphyrazines with annulated 1,4-diazepine heterocycle(s).

References:

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1. Wieczorek E., Mlynarczyk D.T., Kucinska M., Dlugaszewska J., Piskorz J., Popenda L., Szczolko W., Jurga S., Murias M., Mielcarek J., Goslinski T. Eur. J. Med. Chem. 2018, 150, 64–73.
https://doi.org/10.1016/j.ejmech.2018.02.064

2. Tarakanov P.A., Tarakanova E.N., Dorovatovskii P.V., Zubavichus Y.V., Khrustalev V.N., Trashin S.A., De Wael K., Neganova M.E., Mischenko D.V., Sessler J.L., Stuzhin P.A., Pushkarev V.E., Tomilova L.G. Dalton Trans. 2018.
https://doi.org/10.1039/C8DT00384J

3. Wieczorek E., Piskorz J., Popenda L., Jurga S., Mielcarek J., Goslinski T. Tetrahedron Lett. 2017, 58(8), 758–761.
https://doi.org/10.1016/j.tetlet.2017.01.027

4. Tarakanova E.N., Trashin S.A., Simakov A.O., Furuyama T., Dzuban A.V., Inasaridze L.N., Tarakanov P.A., Troshin P.A., Pushkarev V.E., Kobayashi N., Tomilova L.G. Dalton Trans. 2016, 45, 12041–12052.
https://doi.org/10.1039/C6DT01779G

5. Tarakanov P.A., Simakov A.O., Tolbin A.Y., Balashova I.O., Shestov V.I., Tomilova L.G. Spectrochim. Acta, Part A 2015, 139, 464–470.
https://doi.org/10.1016/j.saa.2014.12.054

6. Shvedene N.V., Otkidach K.N., Gumerov M.R., Tarakanov P.A., Tomilova L.G. J. Anal. Chem. 2015, 70, 72–80.
https://doi.org/10.1134/S1061934815010177

7. Tarakanova E.N., Trashin S.A., Tarakanov P.A., Pushkarev V.E., Tomilova L.G. Dyes Pigm. 2015, 117, 61–63.
https://doi.org/10.1016/j.dyepig.2015.02.003

8. Tarakanova E.N., Levitskiy O.A., Magdesieva T.V., Tarakanov P.A., Pushkarev V.E., Tomilova L.G. New J. Chem. 2015, 39, 5797–5804.
https://doi.org/10.1039/C5NJ00884K

9. Piskorz J., Konopka K., Düzgüneş N., Gdaniec Z., Mielcarek J., Goslinski T. ChemMedChem 2014, 9(8), 1775–1782.
https://doi.org/10.1002/cmdc.201402085

10. Tarakanova E.N., Tarakanov P.A., Pushkarev V.E., Tomilova L.G. J. Porphyrins Phthalocyanines 2014, 18, 149–154.
https://doi.org/10.1142/S1088424613501113

11. Khelevina O.G., Ishutkina M.V., Malyasova A.S. Russ. J. Gen. Chem. 2013, 83(8), 1548–1555.
https://doi.org/10.1134/S1070363213080136

12. Malyasova A.S., Kokareva E.A., Tarakanov P.A., Aleksandriiskii V.V., Khelevina O.G., Koifman O.I. Russ. J. Org. Chem. 2013, 49, 1812–1818.
https://doi.org/10.1134/S1070428013120178

13. Piskorz J., Tykarska E., Gdaniec M., Goslinski T., Mielcarek J. Inorg. Chem. Commun. 2012, 20, 13–17.
https://doi.org/10.1016/j.inoche.2012.02.001

14. Tomachynskyi S., Tomachynska L., Tretyakova I., Chernii V. Funct. Mater. 2012, 19, 121–125.

15. Stuzhin P.A., Tarakanov P., Shiryaeva S., Zimenkova A., Koifman O.I., Viola E., Donzello M.P., Ercolani C. J. Porphyrins Phthalocyanines 2012, 16, 968–976.
https://doi.org/10.1142/S1088424612501052

16. Goslinski T., Piskorz J., Brudnicki D., White A.J.P., Gdaniec M., Szczolko W., Tykarska E. Polyhedron 2011, 30, 1004–1011.
https://doi.org/10.1016/j.poly.2010.12.049

17. Tarakanov P.A., Donzello M.P., Koifman O.I., Stuzhin P.A. Macroheterocycles 2011, 4(3), 177–183.
https://doi.org/10.6060/mhc2011.3.06

18. Knyukshto V.N., Kuzmitsky V.A., Borisevich E.A., Volkovich D.I., Bubnova A.S., Stuzhin P.A., Solovyova K.N. J. Appl. Spectrosc. 2009, 76(3), 341–351.
https://doi.org/10.1007/s10812-009-9189-8

19. Donzello M.P., Ercolani C., Mannina L., Viola E., Bubnova A., Khelevina O.G., Stuzhin P.A. Aust. J. Chem. 2008, 61, 262–272.
https://doi.org/10.1071/CH08071

20. Donzello M.P., Dini D., D'Arcangelo G., Ercolani C., Zhan R., Ou Z., Stuzhin P.A., Kadish K.M. J. Am. Chem. Soc. 2003, 125, 14190–14204.
https://doi.org/10.1021/ja0344361

21. Baum S.M., Trabanco A.A., Montalban A.G., Micallef A.S., Zhong C., Meunier H.G., Suhling K., Phillips D., White A.J.P., Williams D.J., Barrett A.G.M., Hoffman B.M. J. Org. Chem. 2003, 68, 1665–1670.
https://doi.org/10.1021/jo026484u

22. Donzello M.P., Ercolani C., Stuzhin P.A., Chiesi-Villa A., Rizzoli C. Eur. J. Inorg. Chem. 1999, 2075–2084.
https://doi.org/10.1002/(SICI)1099-0682(199911)1999:11<2075::AID-EJIC2075>3.0.CO;2-X

23. Begland R.W., Hartter D.R., Jones F.N., Sam D.J., Sheppard W.A., Webster O.W., Weigert F.J. J. Org. Chem. 1974, 39, 2341–2350.
https://doi.org/10.1021/jo00930a004

24. Horiguchi E., Shirai K., Jaung J., Furusyo M., Takagi K., Matsuoka M. Dyes Pigm. 2001, 50, 99–107.
https://doi.org/10.1016/S0143-7208(01)00031-6

25. Horiguchi E., Shirai K., Matsuoka M., Matsui M. Dyes Pigm. 2002, 53, 45–55.
https://doi.org/10.1016/S0143-7208(01)00099-7

26. Horiguchi E., Matsumoto S., Funabiki K., Matsui M. Bull. Chem. Soc. Jpn. 2005, 78, 1167–1173.
https://doi.org/10.1246/bcsj.78.1167

27. Tarakanov P.A., Simakov A.O., Dzuban A.V., Shestov V.I., Tarakanova E.N., Pushkarev V.E., Tomilova L.G. Org. Biomol. Chem. 2016, 14, 1138–1146.
https://doi.org/10.1039/C5OB02098K

28. Carlson R., Nilsson A., Strömqvist M. Acta Chem. Scand. 1982, B37, 7–13.

29. Carlson R., Nilsson A. Acta Chem. Scand. 1984, B38, 49–53.
https://doi.org/10.3891/acta.chem.scand.38b-0049

30. Carlson R., Larsson U., Hansson L. Acta Chem. Scand. 1992, 46, 1211–1214.
https://doi.org/10.3891/acta.chem.scand.46-1211

31. Bonnett R., Okolo K. J. Porphyrins Phthalocyanines 1999, 3, 530–536.
https://doi.org/10.1002/(SICI)1099-1409(199908/10)3:6/7<530::AID-JPP171>3.0.CO;2-Q

32. Lyubimtsev A.V., Zheglova N.V., Smirnova E.N., Syrbu S.A. Russ. Chem. Bull., Int. Ed. 2015, 64(8), 1933–1941.

33. Oliver S.W., Smith T.D. J. Chem. Soc., Perkin Trans. 2 1987, 0, 1579–1582.
https://doi.org/10.1039/p29870001579

34. Stuzhin P.A., Pimkov I.V., Ul'-Khak A., Ivanova S.S., Popkova I.A., Volkovich D.I., Kuz'mitskii V.A., Donzello M.-P. Russ. J. Org. Chem. 2007, 43, 1854.

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A Sterically Driven Approach to the Efficient Synthesis of Low-Symmetry 1,4-Diazepinoporphyrazines

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