Metal-Organic Frameworks as Efficient Catalytic Systems for the Synthesis of 1,5-Benzodiazepines from 1,2-Phenylenediamine and Ketones
Научная публикация
| Общая информация |
Язык:
Английский,
Жанр:
Статья (Full article),
Статус опубликования:
Опубликована,
Оригинальность:
Оригинальная
|
| Журнал |
Journal of Catalysis
ISSN: 0021-9517
, E-ISSN: 1090-2694
|
| Вых. Данные |
Год: 2017,
Том: 354,
Страницы: 128-137
Страниц
: 10
DOI:
10.1016/j.jcat.2017.08.009
|
| Ключевые слова |
1,2-Phenylenediamine, 1,5-Benzodiazepine, Acidity, Ketones, Metal-organic framework, MIL-100 |
| Авторы |
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
|
| Организации |
| 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
|
|
Информация о финансировании (2)
|
1
|
National Research Foundation of Korea
|
2017R1A2B2008774
|
|
2
|
Федеральное агентство научных организаций России
|
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.