Prins cyclisation of (-)-isopulegol with benzaldehyde over ZSM-5 based micro-mesoporous catalysts for production of pharmaceuticals

doi:10.1016/S1872-2067(19)63305-X

Chinese Journal of Catalysis ›› 2019, Vol. 40 ›› Issue (11): 1713-1720.DOI: 10.1016/S1872-2067(19)63305-X

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Prins cyclisation of (-)-isopulegol with benzaldehyde over ZSM-5 based micro-mesoporous catalysts for production of pharmaceuticals

Ekaterina Kholkina^a, Paivi Maki-Arvela^a, Chloe Lozachmeuer^a, Roman Barakov^b, Nataliya Shcherban^b, Dmitry Yu. Murzin^a

a Johan Gadolin Process Chemistry Centre, Faculty of Science and Engineering, Åbo Akademi University, Turku 20500, Finland;
b L.V. Pisarzhevsky Institute of Physical Chemistry, National Academy of Sciences of Ukraine, 31 pr. Nauky, Kiev 03028, Ukraine

Received:2018-12-07 Revised:2019-01-17 Online:2019-11-18 Published:2019-09-06
Contact: Dmitry Yu. Murzin

Abstract

Abstract: Several ZSM-5 derived micro-mesoporous catalysts were investigated in Prins cyclisation of (-)-isopulegol with benzaldehyde acting as a reactant and a solvent for production of heterocyclic oxygen containing 2H-chromene derivatives including the tetrahydropyran structure and exhibiting biological activity. The investigated catalysts were characterized by nitrogen adsorption, ammonia temperature programmed desorption, adsorption-desorption of pyridine and 2,6-di-tert-butylpyridine with Fourier transform infrared spectroscopic control. For the Prins reaction performed at 70℃, the highest yield of the desired product, equal to 67% at complete conversion of (-)-isopulegol, was obtained over a micro-mesoporous catalyst containing an optimum amount of strong acid sites and mesopores, being 12 fold larger than the size of the desired product.

Key words: Micro-mesoporous material, Prins cyclisation, Tetrahydropyran

Ekaterina Kholkina, Paivi Maki-Arvela, Chloe Lozachmeuer, Roman Barakov, Nataliya Shcherban, Dmitry Yu. Murzin. Prins cyclisation of (-)-isopulegol with benzaldehyde over ZSM-5 based micro-mesoporous catalysts for production of pharmaceuticals[J]. Chinese Journal of Catalysis, 2019, 40(11): 1713-1720.

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References

[1] O. S. Patrusheva, K. P. Volcho, N. F. Salakhutdinov, Russ. Chem. Rev., 2018, 87, 771-796.
[2] S. Slater, P. B. Lasonkar, S. Haider, M. J. Alqahtani, A. G. Chittiboy-ina, I. A. Khan, Tetrahedron Lett., 2018, 59, 807-810.
[3] I. V. Ilina, K. P. Volcho, Z. V. Viktorovich, N. F. Salakhutdinov, RU 2664728 C1, 2006.
[4] I. V. Ilyina, V. V. Zarubaev, I. N. Lavrentina, A. A. Shtro, I. L. Esaulkova, D. V. Korchagina, S. S. Borisevich, K. P. Volcho, N. F. Salakhutdinov, Bioorg. Med. Chem. Lett., 2018, 28, 2061-2067.
[5] A. Y. Sidorenko, A. V. Kravtsova, J. Wärnå, A. Aho, I. Heinmaa, I.V. Il'ima, Q. V. Ardashov, K. P. Volcho, N. F. Salakhutdinov, D. Y. Murzin, V. E. Agabekov, Mol. Catal., 2018, 453, 139-148.
[6] K. R. Kishore Kumar Reddy, I. M. L. Rosa, A. C. Doriguetto, E. L. Bastos, L. F. Siulva, Molecules, 2013, 18, 11100-11130.
[7] B. Sarmah, G. Baihya, R. K. Baruah, Eur. J. Org. Chem., 2014, 2014, 7561-7565.
[8] K. R. Kishore, K. Reddy, L. F. Silva Jr, J. Braz. Chem. Soc., 2013, 24, 9, 1414-1419.
[9] G. Baishya, B. Sarmah, N. Hazarika, Synlett, 2013, 24, 1137-1141.
[10] M. N. Timofeeva, V. N. Pancheno, K. P. Volcho, S. V. Zakusin, V. V. Krupskaya, A. Gil, O. S. Mikhalchenko, J. Mol Catal. A, 2016, 414, 160-166.
[11] M. Stekrova, P. Mäki-Arvela, N. Kumar, E. Behvaresh, A. Aho, Q. Balme, K. P. Volcho, N. F. Salakhutdinov, D. Y. Murzin, J. Mol. Catal. A, 2015, 410, 260-270.
[12] M. Stekrova, P. Mäki-Arvela, E. Leino, K. M. Valkaj, K. Eränen, A. Aho, A. Smeds, N. Kumar, K. P. Volcho, N. F. Salakhutdinov, D. Y. Murzin, Catal. Today, 2017, 279, 56-62.
[13] A. Torozova, P. Mäki-Arvela, A. Aho, N. Kumar, A. Smeds, M. Peurla, R. Sjöholm, I. Heinmaa, D. V. Korchagina, K. P. Volcho, N. F. Salakhutdinov, D. Y. Murzin, J. Mol. Catal. A, 2015, 397, 48-55.
[14] S. Yu. Kurbakova, I. V. Il'ina, A. Pavlona, D. Korchagina, O. Yarovaya, T. Tolstikova, K. P. Volcho, N. F. Salakhutdinov, Med. Chem. Res., 2014, 23, 1709-1717.
[15] I. V. Il'ina, D. V. Korshagina, K.P. Volcho, N. F. Salakhutdinov, G. A. Tolstikov, Russ. J. Org. Chem., 2010, 46, 1002-1005.
[16] N. D. Shcherban, R. Y. Barakov, P. Mäki-Arvela, S. A. Sergiienko, I. Bezverkhyy, K. Eränen, D. Y. Murzin, Appl. Catal. A, 2018, 60, 236-247.
[17] R. Barakov, N. Shcherban, P. Yaremov, S. Gryn, V. Solomakha, I. Bezverkhyy, N. Kasian, V. Ilyin, J. Mater. Sci., 2016, 51, 4002-4020.
[18] R. Y. Barakov, N. D. Shcherban, P. S. Yaremov, S. M. Filomenko, V. V. Tsyrina, V. G. Ilyin, Theor. Exp. Chem., 2017, 53, 60-68.
[19] K. Na, M. Choi, W. Park, Y. Sakamoto, O. Terasaki, R. Ryoo, J. Am. Chem. Soc., 2010, 132, 4169-4177.
[20] K. Kim, R. Ryoo, H. D. Jang, M. Choi, J. Catal., 2012, 288, 115-123.
[21] R. Barakov, N. Shcherban, P. Yaremov, I. Bezverkhyy, A. Baranchikov, V. Trachevskii, V. Tsyrina, V. Ilyin, Microporous Mesoporous Mater., 2017, 237, 90-107.
[22] S. Wu, Y. Han, Y. C. Zou, J. W. Song, L. Zhaoi, Y. Di, S. Z. Liu, F. S. Xiao, Chem. Mater., 2004, 16, 486-492.
[23] C. E. A. Kirschhock, R. Ravishankar, F. Verspeurt, P. J. Grobet, P. A. Jacobs, J. A. Martens, J. Phys. Chem. B, 1999, 103, 4965-4971.
[24] K. Góra-Marek, K. Tarach, M. Choi, J. Phys. Chem. C, 2014, 118, 12266-12274.
[25] D. H. Olson, G. T. Kokotallo, S. L. Lawton, J. Phys. Chem., 1991, 85, 2238-2243.

Prins cyclisation of (-)-isopulegol with benzaldehyde over ZSM-5 based micro-mesoporous catalysts for production of pharmaceuticals

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