1,5-Benzodiazepine synthesis via cyclocondensation of 1,2-diamines with ketones using iron-based metal-organic framework MOF-235 as an efficient heterogeneous catalyst

被引:40
作者
Le, Thuan D. [1 ]
Nguyen, Khoa D. [1 ]
Nguyen, Vu T. [1 ]
Truong, Thanh [1 ]
Phan, Nam T. S. [1 ]
机构
[1] HCMC Univ Technol, VNU HCM, Dept Chem Engn, 268 Ly Thuong Kiet,Dist 10, Ho Chi Minh City, Vietnam
关键词
Metal-organic framework; MOF-235; 1,5-Benzodiazepine; 1,2-Phenylenediamine; Heterogeneous catalyst; C-H ACTIVATION; TERMINAL ALKYNES; PROPARGYLAMINE SYNTHESIS; COUPLING REACTIONS; AEROBIC OXIDATION; DERIVATIVES; ACID; NANOPARTICLES; SILICA; MOFS;
D O I
10.1016/j.jcat.2015.10.026
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A crystalline iron-based metal-organic framework MOF-235 was synthesized, and characterized by X-ray powder diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), atomic absorption spectrophotometer (AAS), and nitrogen physisorption measurements. The MOF-235 could be used as a heterogeneous catalyst for the synthesis of 1,5-benzodiazepines by the cyclocondensation of 1,2-diamines with ketones. Excellent conversions to 1,5-benzodiazepines were achieved in the presence of 5 mol% MOF-235 catalyst using molecular oxygen in air as the stoichiometric oxidant. The Fe-MOF exhibited higher catalytic activity for the cyclocondensation reaction than those of other MOFs including MOF-5, Mn(BDC), MOF-199, and Ni-2(BDC)(2)(DABCO). The Fe-MOF catalyst could be separated from the reaction mixture by centrifugation, and could be recovered and reused several times without a significant degradation in catalytic activity. To the best of our knowledge, 1,5-benzodiazepines were not previously synthesized using MOFs as heterogeneous catalysts. (C) 2015 Elsevier Inc. All rights reserved.
引用
收藏
页码:94 / 101
页数:8
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