Triazole- and Thiadiazolecontaining Macroheterocycles: Review of Main Achievements for Last Decade

Yu. V. Suvorova,^a@ T. V. Kustova,^a E. A. Danilova,^a and M. N. Mileeva^b

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

^bIvanovo State Medical Academy, 153012 Ivanovo, Russia

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

DOI: 10.6060/mhc200494s
Macroheterocycles 2020 13(3) 234-239

The work reviews main achievements of last decade in the field of synthesis and properties research of macroheterocyclic compounds of ABBB- and AABAAB-types, A being 1,2,4-triazole, 1,2,4- or 1,3,4-thiadiazole moiety, and B being(un)substituted isoindoline resudie. All the compounds were obtained through interactions between heterocyclic diamine and 1,3-diiminoisoindoline or phthalonitrile under different conditions. The ABBB-type target products have properties of “molecular chameleons”; in other words, they possess an unique ability to postsynthetically modify the molecular optic properties. The AABAAB-type products as macroheterocyclic compounds with an expanded coordination cavity allow to insert one large and several smaller metal atoms into an intramolecular cavity. Therefore, the compounds become potential anion receptors. Moreover, a bathochromic shift of maximum absorption band into infra-red region of electron spectra of AABAAB macroheterocycles with expanded conjugated π-electron system can promotetheir use as photodynamic therapeutic agents.

References:

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1. Elvidge J.A., Linstead R.P. J. Chem. Soc. 1952, 20, 5008-5012.
https://doi.org/10.1039/jr9520005008

2. Pat. 2765308 USA. 1956.

3. Torre de la G., Torres T. J. Org. Chem. 1996, 61, 6446-6449.
https://doi.org/10.1021/jo960704k

4. Danilova E.A., Melenchuk T.V., Trukhina O.N., Zakharov A.V., Islyaikin M.K. Macroheterocycles 2010, 3, 33-37.
https://doi.org/10.6060/mhc2010.1.33

5. Islyaikin M.K., Danilova E.A., Yagodarova L.D., Rodríguez-Morgade M.S., Torres T. Org. Lett. 2001, 3, 2153-2156.
https://doi.org/10.1021/ol015924l

6. Islyaikin M.K., Rodríguez-Morgade M.S., Torres T. Eur. J. Org. Chem. 2002, 2460-2464.
https://doi.org/10.1002/1099-0690(200208)2002:15<2460::AID-EJOC2460>3.0.CO;2-H

7. Sessler J.L., Seidel D. Angew. Chem. Int. Ed. 2003, 42, 5134-5175.
https://doi.org/10.1002/anie.200200561

8. Sessler J.L., Gale P.A., Cho W.S. In: Anion Receptor Chemistry (Stoddart J.F., Ed.) Cambridge: Royal Society of Chemistry, 2006. 430 p.

9. Yoon Z.S., Kwon J.H., Yoon M., Koh M.K., Noh S.B., Sessler J.L., Lee J.T., Seidel D., Aguilar A., Shimizu S., Suzuki M., Osuka A., Kim D. J. Am. Chem. Soc. 2006, 128, 14128-14134.
https://doi.org/10.1021/ja064773k

10. Borodkin V.F., Kolesnikov N.A. Khim. Geterotsikl. Soed. [Chem. Heterocycl. Compds.] 1971, 2, 194-195. (in Russ.).

11. Kolesnikov N.A., Borodkin V.F. Zh. Priklad. Spektrosk. [J. Appl. Spectrosc.] 1971, 14(6), 1124-1127 (in Russ.).
https://doi.org/10.1007/BF00606834

12. Kolesnikov N.A., Borodkin V.F. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 1972, 15(6), 880-882 (in Russ.).

13. Islyaikin M.K., Borodkin V.F., Danilova E.A., Konovalov S.P., Panov A.A. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 1990, 33(6), 18-21 (in Russ.).

14. Kobayashi N., Inagaki S., Nemykin V.N., Nonomura T. Angew. Chem. Int. Ed. 2001, 40, 2710-2712.
https://doi.org/10.1002/1521-3773(20010716)40:14<2710::AID-ANIE2710>3.0.CO;2-A

15. Zakharov A.V., Shlykov S.A., Danilova E.A., Krasnov A.V., Islyaikin M.K., Girichev G.V. Phys. Chem. Chem. Phys. 2009, 11, 8570-8579.
https://doi.org/10.1039/b905436g

16. Trukhina O.N., Rodríguez-Morgade M.S., Wolfrum S., Caballero E., Snejko N., Danilova E.A., Gutiérrez-Puebla E., Islyaikin M.K., Guldi D.M., Torres T. J. Am. Chem. Soc. 2010, 132, 12991-12999.
https://doi.org/10.1021/ja104577d

17. Zakharov A.V., Shlykov S.A., Bumbina N.V., Danilova E.A., Krasnov A.V., Islyaikin M.K., Girichev G.V. Chem. Commun. 2008, 30, 3573-3575.
https://doi.org/10.1039/b804308f

18. Rodríguez-Morgade M.S., Cabezón B., Esperanza S., Torres T. Chem. Eur. J. 2001, 7, 2407-2413.
https://doi.org/10.1002/1521-3765(20010601)7:11<2407::AID-CHEM24070>3.0.CO;2-1

19. Lindman S.V., Shklover V.E., Struchkov Yu.T., Ponomarev I.I., Siling S.A., Vinogradova S.V., Korshak V.V. Izv. Akad. Nauk SSSR Ser. Khim. 1984, 2015-2022 (in Russ.).

20. Kudrik E.V., Islyaikin M.K., Smirniv R.P. Zh. Org. Khim. 1996, 66(9), 1564-1566 (in Russ.).

21. Pat. 2134270 RF, 1999.

22. Hołyńska M., Kubiak M. Acta Cryst. 2008, C64, о609-о612.
https://doi.org/10.1107/S0108270108032769

23. Danilova E.A., Melenchuk T.V., Trukhina O.N., Islyaikin M.K. Macroheterocycles 2010, 3, 68-81.
https://doi.org/10.6060/mhc2010.1.68

24. Tyutina M.A., Kudayarova T.V., Danilova E.A. Russ. J. Gen. Chem. 2017, 87, 1737-1741.
https://doi.org/10.1134/S1070363217080175

25. Elvidge J.A., Linstead R.P. J. Chem. Soc. 1955, 3536-3544.
https://doi.org/10.1039/jr9550003536

26. Sanchez R., Vest G., Scott W., Engel P.S. J. Org. Chem. 1989, 54, 4026-4027.
https://doi.org/10.1021/jo00278a009

27. Vinogradov S.V., Ulitin M.V., Lefedova O.V. Russ. J. Phys. Chem. A 1999, 73, 1741.

28. Kudayarova T.V., Danilova E.A., Koifman O.I. Russ. Chem. Bull. 2018, 12, 2262-2265.
https://doi.org/10.1007/s11172-018-2367-1

29. Butina Yu.V., Kudayarova T.V., Danilova E.A., Semenishin N.N. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2016, 59(10), 36-40.
https://doi.org/10.6060/tcct.20165910.5438

30. Safonova E.A., Martynov A.G., Nefedov S.E., Kirakosyan G.A., Gorbunova Y.G., Tsivadze A.Yu. Inorg. Chem. 2016, 55, 2450−2459.
https://doi.org/10.1021/acs.inorgchem.5b02831

31. Butina Yu.V., Danilova E.A., Kudayarova T.V., Malyasova A.S. Macroheterocycles 2018, 11, 59-66.
https://doi.org/10.6060/mhc180166d

32. Kydayarova T.V., Danilova E.A., Islyaikin M.K., Semenishin N.N., Rusakova N.V. Russ. J. Gen. Chem. 2014, 84, 1706-1710.
https://doi.org/10.1134/S1070363214090114

33. Islyaikin M.K., Danilova E.A., Kudrik E.V., Smirnov R.P., Budunova A.P., Kinzirskii A.S. Pharm. Chem. J. 1997, 31(8), 409-412.
https://doi.org/10.1007/BF02464352

34. Maslova I.P. Chemical Dopands to Polymers. Moscow: Chemisrty, 1981. p. 264 (in Russ.)

35. Filatov M.S., Kydayarova T.V., Danilova E.A., Islyaikin M.K. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 2014, 57(7), 21-25 (in Russ.).

36. Filatov M.S. The Study of the Spatial Structure of the AAAABtype Macroheterocyclic Compound by DFT Method. In: Quantum-chemical Calculations: Structure and Reactivity of Organic and Inorganic Molecules. Ivanovo: ISUCT, 2011. 272 p. (in Russ.)

38. Siling S.A. In: Advances in Porphyrin Chemistry, Vol. 2. St. Petersburg: NII Khimii SpbGU, 1999. p. 320-329 (in Russ.)

39. Butina Yu.V., Danilova E.A., Kudayarova T.V. Macroheterocycles 2016, 9, 206-211.
https://doi.org/10.6060/mhc160526d

40. Zhurko G.A. ChemCraft version 1.6, build 312, http://www. chemcraflprog.com/index.html.

41. Granovsky A.A. Firefly version 8.1.0, build number 9035, http://classic.chem.msu.su/gran/firefly/index.html.

42. Filatov M.S. Synthesis and Properties of the Azolmacroheterocyclic Compounds with Expanded Coordination Cavity. Diss. Cand. Chem. Sci. Ivanovo: ISUCT, 2014. 140 p. (in Russ.).

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Triazole- and Thiadiazolecontaining Macroheterocycles: Review of Main Achievements for Last Decade

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