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Iron-containing materials as catalysts for the synthesis of 1,5-benzodiazepine from 1,2-phenylenediamine and acetone

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Abstract

The cyclocondensation of 1,2-phenylenediamine (I) with acetone was investigated in the presence of Fe-containing microporous nickel phosphate molecular sieves (Fe-VSB-5) and Fe-containing mesoporous mesophase materials (Fe-MMM). The main product was 2,3-dihydro-2,2,4-trimethyl-1H-1,5-benzodiazepine (1,5-benzodiazepine) with 86–88% yield at 50 °C, with an acetone/(I) molar ratio of 2.5 in methanol as the reaction medium. The Fe content was found to affect not only the reaction rate but also yield of 1,5-benzodiazepine. The high reaction rate and yield of 1,5-benzodiazepine were—achieved with isolated iron sites in frameworks of Fe-VSB-5 and Fe-MMM.

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Acknowledgements

This work was conducted within the framework of budget Project No. 0303-2016-0007 for Boreskov Institute of Catalysis and was supported by Kyungpook National University Research Fund, 2016. Textural properties were characterized within the framework of budget Project No. 0303-2016-0002 for Boreskov Institute of Catalysis. Authors thanks Dr. A.V. Toktarev for synthesis of H-ZSM-5 and zeolite-β.

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Authors and Affiliations

  1. Boreskov Institute of Catalysis SB RAS, Prospekt Akad. Lavrentieva 5, 630090, Novosibirsk, Russian Federation

    Maria N. Timofeeva, Sergey A. Prikhod’ko, Kristina N. Makarova, Mikhail E. Malyshev, Valentina N. Panchenko & Artem B. Ayupov

  2. Novosibirsk State Technical University, Prospekt K. Marksa 20, 630092, Novosibirsk, Russian Federation

    Maria N. Timofeeva, Kristina N. Makarova & Valentina N. Panchenko

  3. Department of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, Sankyuck-Dong, Buk-Ku, Daegu, 41566, Republic of Korea

    Sung Hwa Jhung

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  1. Maria N. Timofeeva
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  2. Sergey A. Prikhod’ko
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  3. Kristina N. Makarova
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  4. Mikhail E. Malyshev
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  5. Valentina N. Panchenko
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  6. Artem B. Ayupov
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  7. Sung Hwa Jhung
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Correspondence to Maria N. Timofeeva.

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Timofeeva, M.N., Prikhod’ko, S.A., Makarova, K.N. et al. Iron-containing materials as catalysts for the synthesis of 1,5-benzodiazepine from 1,2-phenylenediamine and acetone. Reac Kinet Mech Cat 121, 689–699 (2017). https://doi.org/10.1007/s11144-017-1190-2

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  • DOI: https://doi.org/10.1007/s11144-017-1190-2

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