Design of Novel Catalysts for Synthesis of 1,5-Benzodiazepines from 1,2-Phenylenediamine and Ketones: NH2-MIL-101(Al) as Integrated Structural Scaffold for Catalytic Materials Based on Calix[4]arenes | Sciact - CRIS-system of Boreskov Institute of Catalysis

Design of Novel Catalysts for Synthesis of 1,5-Benzodiazepines from 1,2-Phenylenediamine and Ketones: NH2-MIL-101(Al) as Integrated Structural Scaffold for Catalytic Materials Based on Calix[4]arenes Full article

Journal

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

Output data

Year: 2019, Volume: 369, Pages: 60-71 Pages count : 12 DOI: 10.1016/j.jcat.2018.10.035

Tags

Metal-organic framework NH2-MIL-101(Al); Calix[4]arenes; 1,5-Benzodiazepine; 1,2-Phenylenediamine; Ketones

Authors

Isaeva Vera I. ^1,2 , Timofeeva Maria N. ^3,4 , Panchenko Valentina N. ³ , Lukoyanov Ivan A. ^3,4 , Chernyshev Vladimir V. ^5,6 , Kapustin Gennady I. ¹ , Davshan Nikolai A. ¹ , Kustov Leonid M. ^1,2,4

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, RAS, Leninsky Prospect 47, Moscow 119991, Russian Federation
2	National University of Science and Technology MISiS, Leninsky Pospect 4, 119991, Russian Federation
3	Boreskov Institute of Catalysis SB RAS, Prospekt Akad. Lavrentieva 5, 630090 Novosibirsk, Russian Federation
4	Novosibirsk State Technical University, pr. K. Marks 20, 630092 Novosibirsk, Russian Federation
5	Department of Chemistry, M.V. Lomonosov Moscow State University, 1-3 Leninskie Gory, Moscow 119991, Russian Federation
6	A. N. Frumkin Institute of Physical Chemistry and Electrochemistry RAS, 31 Leninsky Prospect, Moscow 119071, Russian Federation

Funding (2)

1	Federal Agency for Scientific Organizations	0303-2016-0007
2	The Ministry of Education and Science of the Russian Federation	K1-2015-045

Novel nanoporous composites (MIL/K-SO3H and MIL/Ks-CN) were synthesized by the encapsulation of para-sulfonatocalix[4]arene (K-SO3H) and para-tert-butylthiacalix[4]arene (Ks-CN) with strong (SO3H) and weak (CN) acidic functionalities, respectively, in the aluminum(III) 2-aminoterephthalate metal organic framework (NH2-MIL-101(Al)) cavities. MIL/K-SO3H and MIL/Ks-CN materials were prepared by microwave assisted one-step synthesis in situ following to the ship in a bottle approach. According to comprehensive study, textural properties, the morphology and particle sizes of composites depend on the type of the embedded calix[4]arene molecules. Catalytic properties of MIL/K-SO3H and MIL/Ks-CN composites were investigated in the synthesis of physiologically active 1,5-benzodiazepines from 1,2-phenylenediamine and ketones (acetone, acetophenone, methyl ethyl ketone). It was found that their catalytic activity can be adjusted by surface acidity, which depends on the nature of the interactions between functional substituents in the arene “bowl” of calix[4]arenes and NH2 groups in organic linkers of NH2-MIL-101(Al) framework.

Isaeva V.I. , Timofeeva M.N. , Panchenko V.N. , Lukoyanov I.A. , Chernyshev V.V. , Kapustin G.I. , Davshan N.A. , Kustov L.M.
Design of Novel Catalysts for Synthesis of 1,5-Benzodiazepines from 1,2-Phenylenediamine and Ketones: NH2-MIL-101(Al) as Integrated Structural Scaffold for Catalytic Materials Based on Calix[4]arenes
Journal of Catalysis. 2019. V.369. P.60-71. DOI: 10.1016/j.jcat.2018.10.035 WOS Scopus РИНЦ AN OpenAlex

Submitted:	Aug 28, 2018
Accepted:	Oct 29, 2018
Published online:	Nov 14, 2018
Published print:	Jan 1, 2019

Web of science:	WOS:000460711700007
Scopus:	2-s2.0-85056472337
Elibrary:	38625541
Chemical Abstracts:	2018:2165304
OpenAlex:	W2901591365

DB	Citing
Scopus	24
Web of science	25
Elibrary	24
OpenAlex	25