Synthesis and Application of Imidazolium-Based Ionic Liquid Supported on Hydroxyapatite Encapsulated γ-Fe2O3 Nanocatalyst in Preparation of Pyrido[2,3-d]Pyrimidines

被引：12

作者：

Ramezanzadeh, Forough ^{[1
]}

Mamaghani, Manouchehr ^{[2
]}

Fallah-Bagher Shaidaei, Hossein ^{[1
]}

Sheykhan, Mehdi ^{[2
]}

机构：

[1] Islamic Azad Univ, Rasht Branch, Fac Sci, Dept Chem, Rasht, Iran

[2] Univ Guilan, Fac Sci, Dept Chem, POB 41335-1914, Rasht, Iran

来源：

POLYCYCLIC AROMATIC COMPOUNDS | 2021年 / 41卷 / 09期

关键词：

12-Dimethylimidazole; gamma-Fe2O3; HAp; ionic liquid; magnetic nanocatalyst; pyrido[23-d]pyrimidines; pyrrole; ONE-POT SYNTHESIS; HYBRID MAGNETIC NANOCATALYST; 5-SUBSTITUTED; 1H-TETRAZOLES; DERIVATIVES; COMPLEX; ACID; NANOPARTICLES; GREEN;

D O I：

10.1080/10406638.2019.1705360

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of novel 2-amino-5-aryl-7-(1-methyl-1H-pyrrol-2-yl)-4-oxo-3,4,5,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carbonitrile derivatives is reported by the reaction of 2,6-diaminopyrimidin-4(3H)-one, 3-(1-methy-1H-pyrrol-2-yl)-3-oxopropane nitrile and aryl aldehydes in the presence of newly synthesized imidazolium based ionic liquid supported on hydroxyapatite encapsulated gamma-Fe2O3 nanocatalyst [gamma-Fe2O3@HAp-Si(CH2)(3)Cl@DMIM] in short reaction times (7-13 min) and high to excellent yields (80%-95%). Cleaner reaction profile, mild reaction conditions, use of the green solvent and reusability of the catalyst, make this protocol attractive for the large scale synthesis of pyrido[2,3-d]pyrimidine-6-carbonitrile derivatives and is amenable for iterative combinatorial library generation. The synthesized nanoparticles were characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscope, energy dispersive analysis of X-rays, thermogravimetric analysis, differential thermogravimetric and vibrating sample magnetometer.

引用

页码：1925 / 1943

页数：19

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[21] Hexamethylenetetramine grafted layered double hydroxides as a novel and green heterogeneous ionic liquid catalyst for the synthesis of pyrido[2,3-d]pyrimidine derivatives [J].

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