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

Maria N. Timofeeva; Sergey A. Prikhod’ko; Kristina N. Makarova; Mikhail E. Malyshev; Valentina N. Panchenko; Artem B. Ayupov; Sung Hwa Jhung

doi:10.1007/s11144-017-1190-2

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

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

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

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.

Original language	English
Pages (from-to)	689-699
Number of pages	11
Journal	Reaction Kinetics, Mechanisms and Catalysis
Volume	121
Issue number	2
DOIs	https://doi.org/10.1007/s11144-017-1190-2
State	Published - 1 Aug 2017

Keywords

1,2-Phenylenediamine
1,5-Benzodiazepine
Acetone
Fe-containing mesoporous materials
Fe-VSB-5

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10.1007/s11144-017-1190-2

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

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.",

keywords = "1,2-Phenylenediamine, 1,5-Benzodiazepine, Acetone, Fe-containing mesoporous materials, Fe-VSB-5",

author = "Timofeeva, {Maria N.} and Prikhod{\textquoteright}ko, {Sergey A.} and Makarova, {Kristina N.} and Malyshev, {Mikhail E.} and Panchenko, {Valentina N.} and Ayupov, {Artem B.} and Jhung, {Sung Hwa}",

note = "Publisher Copyright: {\textcopyright} 2017, Akad{\'e}miai Kiad{\'o}, Budapest, Hungary.",

year = "2017",

month = aug,

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doi = "10.1007/s11144-017-1190-2",

language = "English",

volume = "121",

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journal = "Reaction Kinetics, Mechanisms and Catalysis",

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T1 - Iron-containing materials as catalysts for the synthesis of 1,5-benzodiazepine from 1,2-phenylenediamine and acetone

AU - Timofeeva, Maria N.

AU - Prikhod’ko, Sergey A.

AU - Makarova, Kristina N.

AU - Malyshev, Mikhail E.

AU - Panchenko, Valentina N.

AU - Ayupov, Artem B.

AU - Jhung, Sung Hwa

PY - 2017/8/1

Y1 - 2017/8/1

N2 - 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.

AB - 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.

KW - 1,2-Phenylenediamine

KW - 1,5-Benzodiazepine

KW - Acetone

KW - Fe-containing mesoporous materials

KW - Fe-VSB-5

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U2 - 10.1007/s11144-017-1190-2

DO - 10.1007/s11144-017-1190-2

M3 - Article

AN - SCOPUS:85018267591

SN - 1878-5190

VL - 121

SP - 689

EP - 699

JO - Reaction Kinetics, Mechanisms and Catalysis

JF - Reaction Kinetics, Mechanisms and Catalysis

IS - 2

ER -

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

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