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Crystalline and amorphous aluminosilicates with varying pore structures in the synthesis of 1,5-benzodiazepine

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Abstract

The catalytic properties of zeolites (microporous H-Y and granular micro-mesomacroporous H-Yh) and amorphous mesoporous aluminosilicate ASM in the reaction of 1,2-phenylenediamine with acetone were studied. The main reaction product was 2,2,4-trimethyl-2,3-dihydro-1H-1,5-benzodiazepine (selectivity up to 99% at a 94% conversion of 1,2-phenylenediamine). For the synthesis of 1,5-benzodiazepine, the most effective was 0.95H-Yh, a granular zeolite with a hierarchical porous structure. The catalyst demonstrated operational stability for three cycles.

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References

  1. P. Aastha, K. Navneet, A. Anushu, S. Pratima, K. Dharma, Res. J. Chem. Sci., 2013, 3, 90; DOI: https://doi.org/10.1002/chin.201422238.

    Google Scholar 

  2. P. S. Salve, D. S. Mali, Int. J. Pharma. Bio. Sci., 2013, 4, 345–370.

    CAS  Google Scholar 

  3. J. B. Bariwal, K. D. Upadhyay, A. T. Manvar, J. C. Trivedi, J. S. Singh, K. S. Jain, A. K. Shah, Eur. J. Med. Chem., 2008, 43, 2279; DOI: https://doi.org/10.1016/j.ejmech.2008.05.035.

    Article  CAS  PubMed  Google Scholar 

  4. Y. Chen, V. Le, X. Xu, X. Shao, J. Liu, Z. Li, Bioorg. Med. Chem. Lett., 2014, 24, 3948; DOI: https://doi.org/10.1016/j.bmcl.2014.06.041.

    Article  CAS  PubMed  Google Scholar 

  5. S. S. Ilango, P. U. Remya, S. Ponnuswamy, Ind. J. Chem., 2013, 52, 136–140; DOI: https://doi.org/10.1002/chin.201319191.

    Google Scholar 

  6. M. N. Kumaraswamy, V. P. Vaidya, C. Chandrashekhar, D. A. Parthima-Mathias, H. Shivakumar, K. M. Mahadevan, Int. J. Pharm. Chem. Biol. Sci., 2013, 3, 281.

    Google Scholar 

  7. P. Nikas, E. Gatta, A. Cupello, M. Di Braccio, G. Grossi, F. Pellistri, M. Robello, Neurosci., 2013, 243, 158; DOI: https://doi.org/10.1016/j.neuroscience.2013.04.007.

    Article  CAS  Google Scholar 

  8. US Pat. 1,537,757; Chem. Abstr., 1970, 73, 100054w.

  9. J. A. L. Herbert, H. Suschitzky, J. Chem. Soc, Perkin Trans. 1, 1974, 2657–2661.

  10. H. R. Morales, A. Bulbarela, R. Contreras, Heterocycles, 1986, 24, 135.

    Article  Google Scholar 

  11. X. Q. Pan, J. P. Zou, Z. H. Hauang, W. Zhang, Tetrahedron Lett., 2008, 49, 5302; DOI: https://doi.org/10.1016/j.tetlet.2008.06.082.

    Article  CAS  Google Scholar 

  12. V. Sivamurugan, K. Deepa, M. Palanichamy, V. Murugesan, Synth. Commun., 2004, 34, 3833; DOI: https://doi.org/10.1081/SCC-200034752.

    Article  CAS  Google Scholar 

  13. W. Y. Chen, J. Lu, Synlett, 2005, No. 8, 1337; DOI: https://doi.org/10.1055/s-2005-868516.

  14. P. Minothora, S. S. Julia, A. T. Constantinos, Tetrahedron Lett., 2002, 43, 1755; DOI: https://doi.org/10.1016/S0040-4039(02)00115-6.

    Article  Google Scholar 

  15. D. V. Jarikote, S. A. Siddiqui, R. Rajagopal, D. Thomas, R. J. Lahotiands, K. V. Srinivasan, Tetrahedron Lett., 2003, 44, 1835; DOI: https://doi.org/10.1016/S0040-4039(03)00096-0.

    Article  CAS  Google Scholar 

  16. M. Godino-Ojer, I. Matos, M. Bernardo, R. Carvalho, O. S. G. P. Soares, C. Durán-Valle, E. Pérez Mayoral, Catal. Today, 2020, 357, 64; DOI: https://doi.org/10.1016/j.cattod.2019.11.027.

    Article  CAS  Google Scholar 

  17. M. N. Timofeeva, E. A. Petrova, E. A. Mel’gunova, A. Gil, M. A. Vicente, V. N. Panchenko, React. Kinet. Mech. Catal., 2019, 127, 41; DOI: https://doi.org/10.1007/s11144-018-1454-5.

    Article  CAS  Google Scholar 

  18. B. González, R. Trujillano, M. A. Vicente, A. Gil, V. N. Panchenko, E. A. Petrova, M. N. Timofeeva, Appl. Clay Sci., 2017, 146, 15, 388; DOI: https://doi.org/10.1016/j.clay.2017.06.028.18.

    Article  Google Scholar 

  19. A. Primo, H. Garcia, Chem. Soc. Rev., 2014, 43, 7548; DOI: https://doi.org/10.1039/C3CS60394F.

    Article  CAS  PubMed  Google Scholar 

  20. B. M. Weckhuysen, J. Yu, Chem. Soc. Rev., 2015, 44, 7022; DOI: https://doi.org/10.1039/C5CS90100F.

    Article  CAS  PubMed  Google Scholar 

  21. A. Hegedüs, Z. Hell, A. Potor, Catal. Lett., 2005, 105, 229; DOI: https://doi.org/10.1007/s10562-005-8695-4.

    Article  Google Scholar 

  22. M. Firdaus, M. D. Prameswari, Bull. Chem. React. Eng. Catal., 2019, 14, 9; DOI: https://doi.org/10.9767/bcrec.14.1.2222.9-16.

    Article  CAS  Google Scholar 

  23. M. Tajbakhsh, M. M. Heravi, B. Mohajerani, A. N. Ahmadi, J. Mol. Catal. A Chem., 2006, 247, No. 1–2, 213; DOI: https://doi.org/10.1016/j.molcata.2005.11.033.

    Article  CAS  Google Scholar 

  24. M. J. Climent, A. Corma, S. Iborra, L. L. Santos, Chem. Eur. J., 2009, 15, 8834; DOI: https://doi.org/10.1002/chem.200900492.

    Article  CAS  PubMed  Google Scholar 

  25. S. A. Majid, W. A. Khanday, R. Tomar, J. Biomed. Biotechnol., 2012, 2012, 1; DOI: https://doi.org/10.1155/2012/510650.

    Article  Google Scholar 

  26. M. Jeganathan, K. Pitchumani, ACS Sustain. Chem. Eng., 2014, 2, 1169; DOI: https://doi.org/10.1021/sc400560v.

    Article  CAS  Google Scholar 

  27. K. Sucheta, B. Vittal Rao, Ind. J. Chem., 2005, 44, 2152; DOI: https://doi.org/10.1002/chin.200605172.

    Google Scholar 

  28. B. I. Kutepov, O. S. Travkina, M. R. Agliullin, A. N. Khazipova, I. N. Pavlova, S. V. Bubennov, S. A. Kostyleva, N. G. Grigor’eva, Petroleum Chemistry, 2019, 59, 297; DOI: https://doi.org/10.1134/S0965544119030095.

    Article  CAS  Google Scholar 

  29. O. S. Travkina, M. R. Agliullin, N. A. Filippova, A. N. Khazipova, I. G. Danilova, N. G. Grigor’eva, N. Narender, M. L. Pavlov, B. I. Kutepov, RSC Adv., 2017, 7, 32581; DOI: https://doi.org/10.1039/C7RA04742H.

    Article  CAS  Google Scholar 

  30. N. G. Grigorieva, S. A. Kostyleva, S. V. Bubennov, V. R. Bikbaeva, A. R. Gataulin, N. A. Filippova, A. N. Khazipova, T. R. Prosochkina, B. I. Kutepov, N. Narender, J. Saudi. Chem. Soc., 2019, 23, 452; DOI: https://doi.org/10.1016/j.jscs.2018.08.011.

    Article  CAS  Google Scholar 

  31. N. G. Grigorieva, N. A. Filippova, A. N. Khazipova, O. S. Travkina, B. I. Kutepov, Kataliz v Prom-sti [Catalysis in Industry], 2015, 15, No. 4, 42 (in Russian); DOI: https://doi.org/10.18412/1816-0387-2015-4-42-48.

    CAS  Google Scholar 

  32. N. G. Grigorieva, N. A. Filippova, S. V. Bubennov, A. N. Khazipova, B. I. Kutepov, V. A. Dyakonov, Petroleum Chemistry, 2021, 61, 364; DOI: https://doi.org/10.1134/S0965544121030075.

    Article  Google Scholar 

  33. N. G. Grigor’eva, S. A. Kostyleva, A. S. Artem’eva, S. V. Bubennov, B. I. Kutepov, Petroleum Chemistry, 2020, 60, 525; DOI: https://doi.org/10.1134/S0965544120040088.

    Article  Google Scholar 

  34. N. G. Grigor’eva, O. S. Travkina, S. V. Bubennov, N. A. Filippova, A. S. Artem’eva, A. V. Bayburtli, R. Z. Kuvatova, B. I. Kutepov, Kinet. Catal., 2022, 63, 781; DOI: https://doi.org/10.1134/S0023158422060052.

    Article  Google Scholar 

  35. N. G. Grigor’eva, A. V. Bayburtli, R. Z. Kuvatova, T. V. Semenova, S. V. Bubennov, G. Z. Raskildina, S. S. Zlotsky, B. I. Kutepov, Russ. Chem. Bull., 2020, 69, 525; DOI: https://doi.org/10.1007/s11172-020-2793-8.

    Article  Google Scholar 

  36. A. J. Gordon, R. A. Ford, The Chemist’s Companion. A Handbook of Practical Data, Techniques, and References, John Wiley and Sons, New York, 1972.

    Google Scholar 

  37. M. L. Pavlov, O. S. Travkina, A. N. Khazipova, R. A. Basimova, N. N. Shavaleeva, B. I. Kutepov, Petroleum Chemistry, 2015, 55, 552; DOI: https://doi.org/10.1134/S0965544115070105.

    Article  CAS  Google Scholar 

  38. M. R. Agliullin, N. G. Grigor’eva, I. G. Danilova, O. V. Magaev, O. V. Vodyankina, Kinet. Catal., 2015, 56, 501; DOI: https://doi.org/10.1134/S0023158415040011.

    Article  CAS  Google Scholar 

  39. M. R. Agliullin, I. G. Danilova, A. V. Faizullin, S. V. Amarantov, S. V. Bubennov, T. R. Prosochkina, N. G. Grigor’eva, E. A. Paukshtis, B. I. Kutepov, Micropor. Mesopor. Mat., 2016, 230, 118; DOI: https://doi.org/10.1016/j.micromeso.2016.05.007.

    Article  CAS  Google Scholar 

  40. S. J. Gregg, K. S. W. Sing, Adsorption, Surface Area and Porosity, 2nd ed., Academic Press, New York, 1982, 304 pp.

    Google Scholar 

  41. A. Auroux, Calorimetry and Thermal Methods in Catalysis, Springer, New York, NY, USA, 2013, 154, 569 pp.

    Book  Google Scholar 

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Funding

The work was performed in the framework of the state assignment of the Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences (Topic No. FMRS-2022-0080). Structural studies were carried out at the Agidel Regional Center for Collective Use of the Ufa Federal Research Center of the Russian Academy of Sciences within the framework of the state assignment of the Institute of Petrochemistry and Catalysis of the Ufa Federal Research Center of the Russian Academy of Sciences (Topic No. FMRS-2022-0081).

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Correspondence to N. G. Grigorieva.

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Dedicated to the memory of Academician of the Russian Academy of Sciences G. A. Tolstikov (1933–2013).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 10, pp. 2357–2365, October, 2023.

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Grigorieva, N.G., Bubennov, S.V., Filippova, N.A. et al. Crystalline and amorphous aluminosilicates with varying pore structures in the synthesis of 1,5-benzodiazepine. Russ Chem Bull 72, 2357–2365 (2023). https://doi.org/10.1007/s11172-023-4033-5

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  • DOI: https://doi.org/10.1007/s11172-023-4033-5

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