Metal-organic frameworks as efficient catalytic systems for the synthesis of 1,5-benzodiazepines from 1,2-phenylenediamine and ketones

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Metal-organic frameworks as efficient catalytic systems for the synthesis of 1,5-benzodiazepines from 1,2-phenylenediamine and ketones. / Timofeeva, M. N.; Panchenko, V. N.; Prikhod'ko, S. A. et al.

In: Journal of Catalysis, Vol. 354, 10.2017, p. 128-137.

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

BibTeX

@article{181ac739dc184d65bb1abccc99611d60,

title = "Metal-organic frameworks as efficient catalytic systems for the synthesis of 1,5-benzodiazepines from 1,2-phenylenediamine and ketones",

abstract = "Benzodiazepines and their derivatives are a very important class of nitrogen-containing heterocyclic compounds with biological activity that are widely used in medicine. In this study, we demonstrated synthesis of 1,5-benzodiazepines from 1,2-phenylenediamine and ketones (acetone, cyclohexanone, acetophenone, methyl ethyl ketone) in the presence of isostructural porous metal-benzenetricarboxylates of the families MIL-100(M) (M: V3+, Al3+, Fe3+ and Cr3+) and three porous aluminium trimesates Al-BTCs (MIL-96(Al), MIL-100(Al) and MIL-110(Al)). A combination of catalytic, theoretical and physicochemical methods showed that reaction rates and yields of 1,5-benzodiazepines were adjusted by the type of metal ions and accessibility of active sites. The yield of 1,5-benzodiazepines in the presence of MIL-100(M) was comparable with zeolites, such as HY, H-ZSM−5, β-zeolite and heulandite.",

keywords = "1,2-Phenylenediamine, 1,5-Benzodiazepine, Acidity, Ketones, Metal-organic framework, MIL-100, SOLVENT-FREE CONDITIONS, MICROWAVE IRRADIATION, CHROMIUM(III) CARBOXYLATE, ACID SITES, NITRILE OXIDES, 1,3-DIPOLAR CYCLOADDITION, HETEROGENEOUS CATALYST, DERIVATIVES, HIGH-YIELD SYNTHESIS, CHLORIDE",

author = "Timofeeva, {M. N.} and Panchenko, {V. N.} and Prikhod'ko, {S. A.} and Ayupov, {A. B.} and Larichev, {Yu V.} and Khan, {Nazmul Abedin} and Jhung, {Sung Hwa}",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Inc.",

year = "2017",

month = oct,

doi = "10.1016/j.jcat.2017.08.009",

language = "English",

volume = "354",

pages = "128--137",

journal = "Journal of Catalysis",

issn = "0021-9517",

publisher = "Academic Press Inc.",

}

RIS

TY - JOUR

T1 - Metal-organic frameworks as efficient catalytic systems for the synthesis of 1,5-benzodiazepines from 1,2-phenylenediamine and ketones

AU - Timofeeva, M. N.

AU - Panchenko, V. N.

AU - Prikhod'ko, S. A.

AU - Ayupov, A. B.

AU - Larichev, Yu V.

AU - Khan, Nazmul Abedin

AU - Jhung, Sung Hwa

PY - 2017/10

Y1 - 2017/10

N2 - Benzodiazepines and their derivatives are a very important class of nitrogen-containing heterocyclic compounds with biological activity that are widely used in medicine. In this study, we demonstrated synthesis of 1,5-benzodiazepines from 1,2-phenylenediamine and ketones (acetone, cyclohexanone, acetophenone, methyl ethyl ketone) in the presence of isostructural porous metal-benzenetricarboxylates of the families MIL-100(M) (M: V3+, Al3+, Fe3+ and Cr3+) and three porous aluminium trimesates Al-BTCs (MIL-96(Al), MIL-100(Al) and MIL-110(Al)). A combination of catalytic, theoretical and physicochemical methods showed that reaction rates and yields of 1,5-benzodiazepines were adjusted by the type of metal ions and accessibility of active sites. The yield of 1,5-benzodiazepines in the presence of MIL-100(M) was comparable with zeolites, such as HY, H-ZSM−5, β-zeolite and heulandite.

AB - Benzodiazepines and their derivatives are a very important class of nitrogen-containing heterocyclic compounds with biological activity that are widely used in medicine. In this study, we demonstrated synthesis of 1,5-benzodiazepines from 1,2-phenylenediamine and ketones (acetone, cyclohexanone, acetophenone, methyl ethyl ketone) in the presence of isostructural porous metal-benzenetricarboxylates of the families MIL-100(M) (M: V3+, Al3+, Fe3+ and Cr3+) and three porous aluminium trimesates Al-BTCs (MIL-96(Al), MIL-100(Al) and MIL-110(Al)). A combination of catalytic, theoretical and physicochemical methods showed that reaction rates and yields of 1,5-benzodiazepines were adjusted by the type of metal ions and accessibility of active sites. The yield of 1,5-benzodiazepines in the presence of MIL-100(M) was comparable with zeolites, such as HY, H-ZSM−5, β-zeolite and heulandite.

KW - 1,2-Phenylenediamine

KW - 1,5-Benzodiazepine

KW - Acidity

KW - Ketones

KW - Metal-organic framework

KW - MIL-100

KW - SOLVENT-FREE CONDITIONS

KW - MICROWAVE IRRADIATION

KW - CHROMIUM(III) CARBOXYLATE

KW - ACID SITES

KW - NITRILE OXIDES

KW - 1,3-DIPOLAR CYCLOADDITION

KW - HETEROGENEOUS CATALYST

KW - DERIVATIVES

KW - HIGH-YIELD SYNTHESIS

KW - CHLORIDE

UR - http://www.scopus.com/inward/record.url?scp=85028724133&partnerID=8YFLogxK

U2 - 10.1016/j.jcat.2017.08.009

DO - 10.1016/j.jcat.2017.08.009

M3 - Article

AN - SCOPUS:85028724133

VL - 354

SP - 128

EP - 137

JO - Journal of Catalysis

JF - Journal of Catalysis

SN - 0021-9517

ER -

ID: 9915967