Metal-Organic Frameworks as Efficient Catalytic Systems for the Synthesis of 1,5-Benzodiazepines from 1,2-Phenylenediamine and Ketones | Sciact - CRIS-system of Boreskov Institute of Catalysis

Metal-Organic Frameworks as Efficient Catalytic Systems for the Synthesis of 1,5-Benzodiazepines from 1,2-Phenylenediamine and Ketones Full article

Journal

Journal of Catalysis
ISSN: 0021-9517 , E-ISSN: 1090-2694

Output data

Year: 2017, Volume: 354, Pages: 128-137 Pages count : 10 DOI: 10.1016/j.jcat.2017.08.009

Tags

1,2-Phenylenediamine, 1,5-Benzodiazepine, Acidity, Ketones, Metal-organic framework, MIL-100

Authors

Timofeeva M.N. ^1,2 , Panchenko V.N. ^1,3 , Prikhodʹko S.A. ^1,3 , Ayupov A.B. ¹ , Larichev Y.V. ^1,2 , Khan Nazmul Abedin ⁴ , Jhung Sung Hwa ⁴

Affiliations

1	Boreskov Institute of Catalysis SB RAS, Prospekt Akad. Lavrentieva 5, 630090 Novosibirsk, Russian Federation
2	Novosibirsk State Technical University, Prospekt K. Marksa 20, 630092 Novosibirsk, Russian Federation
3	Novosibirsk State University, St. Pirogova 2, 630090 Novosibirsk, Russian Federation
4	Department of Chemistry and Green-Nano Materials Research Center, Kyungpook National University, Sankyuck-Dong, Buk-Ku, Daegu 41566, Republic of Korea

Funding (2)

1	National Research Foundation of Korea	2017R1A2B2008774
2	Federal Agency for Scientific Organizations	0303-2016-0007

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.

Timofeeva M.N. , Panchenko V.N. , Prikhodʹko S.A. , Ayupov A.B. , Larichev Y.V. , Khan N.A. , Jhung S.H.
Metal-Organic Frameworks as Efficient Catalytic Systems for the Synthesis of 1,5-Benzodiazepines from 1,2-Phenylenediamine and Ketones
Journal of Catalysis. 2017. V.354. P.128-137. DOI: 10.1016/j.jcat.2017.08.009 WOS Scopus РИНЦ ANCAN OpenAlex

Submitted:	Apr 27, 2017
Accepted:	Aug 9, 2017
Published online:	Sep 6, 2017
Published print:	Oct 1, 2017

Web of science:	WOS:000413283000012
Scopus:	2-s2.0-85028724133
Elibrary:	31078620
Chemical Abstracts:	2017:1430212
Chemical Abstracts (print):	168:337663
OpenAlex:	W2752045689

DB	Citing
Web of science	19
Scopus	19
Elibrary	21
OpenAlex	22