860460-70-4Relevant academic research and scientific papers
Choline chloride/urea as a deep eutectic solvent/organocatalyst promoted three-component synthesis of 3-aminoimidazo-fused heterocycles via Groebke-Blackburn-Bienayme process
Shaabani, Ahmad,Hooshmand, Seyyed Emad
, p. 310 - 313 (2016)
The catalytic activity of urea-, metal- and organic acid-based/choline chloride deep eutectic solvents/organocatalysts was investigated for the synthesis of 3-aminoimidazo-fused heterocycles via a one-pot domino reaction of an aldehyde, an isocyanide and 2-aminoheterocycles. The urea-based/choline chloride system exhibited significant catalytic activity for the reaction and could be reused in four consecutive reactions with no considerable loss in catalytic activity.
Magnetic spent coffee ground as an efficient and green catalyst for aerobic oxidation of alcohols and tandem oxidative Groebke–Blackburn–Bienaymé reaction
Farhid, Hassan,Shaabani, Ahmad
, p. 1199 - 1209 (2020/11/09)
Abstract: In this work, magnetic spent coffee ground as a green, inexpensive, and abundant material was synthesized and characterized by a variety of techniques, including X-ray diffraction pattern, thermal gravimetric analysis, scanning electron microscopy, energy-dispersive spectroscopy, inductively coupled plasma optical emission spectrometry, and Fourier transform infrared spectroscopy. The magnetic spent coffee ground was successfully utilized as a catalyst in aerobic oxidation of primary and secondary benzylic alcohols and tandem oxidative Groebke–Blackburn–Bienaymé reaction. Graphic abstract: [Figure not available: see fulltext.].
Diverse Oxidative C(sp2)-N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α-Ketoamides and N-(pyridin-2-yl)arylamides
Xu, Fangzhou,Wang, Yanyan,Xun, Xiwei,Huang, Yun,Jin, Zhichao,Song, Baoan,Wu, Jian
, p. 8411 - 8422 (2019/05/17)
An efficient and chemoselective C(sp2)-N bond cleavage of aromatic imidazo[1,2-a]pyridine molecules is developed. A broad scope of amide compounds such as α-ketoamides and N-(pyridin-2-yl)arylamides are afforded as the final products in up to quantitative yields. Diverse C-N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some α-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.
Tandem oxidative isocyanide-based cycloaddition reactions in the presence of MIL-101(Cr) as a reusable solid catalyst
Shaabani, Ahmad,Sepahvand, Heshmatollah,Amini, Mostafa M.,Hashemzadeh, Alireza,Borjian Boroujeni, Mahmoud,Badali, Elham
, p. 1832 - 1837 (2018/03/07)
The tandem oxidative three-component synthesis of two types of the heterocycles such as furans and imidazopyridines, via isocyanides [1+4] cycloaddition reactions in the presence of MIL-101(Cr) under aerobic conditions are reported. When the 4-toluenesulfonylmethyl isocyanide was used, an unexpected [3+2] cycloaddition reaction of isocyanides with aldehydes accomplished and dihydrophenyloxazoles and phenyloxazoles produced. These syntheses were successfully carried out using a wide scope of the substrates.
Visible-light-activated C-C and C-N bond formation in the synthesis of imidazo[1,2-: A] pyridines and imidazo[2,1- b] thiazoles under catalyst and solvent-free conditions
Shivhare, Km Neha,Jaiswal, Manish K.,Srivastava, Anushree,Tiwari, Saurabh K.,Siddiqui
, p. 16591 - 16601 (2018/10/24)
The formation of a 3-aminoimidazo-fused heterocyclic compound and its derivatives through a multicomponent one-pot reaction, activated by visible light, is reported. The noticeable feature of this protocol is the utilization of a universally available energy source to activate the reaction. The reported methodology is the first protocol that represents the implementation of visible light for this Ugi-type synthesis from 2-aminoheterocycles, aldehydes, and isocyanides as well as offers the advantages of improved selectivity, outstanding yields, solvent and catalyst-free conditions, environmental sustainability and convenient access to starting materials.
Green synthesis of imidazo[1,2-a]pyridines using calix[6]arene-SO3H surfactant in water
Esmaielzade Rostami, Mahshid,Gorji, Banafsheh,Zadmard, Reza
, p. 2393 - 2398 (2018/05/25)
In this research, green synthesis of imidazo[1,2-a]pyridines in the presence of calix[n]arenes-SO3H as a Br?nsted acid catalyst and surfactant is described. Using of calix[n]arenes in water provided a hydrophobic cavity that successfully carried out the synthesis reactions at short times with high yields. This catalyst system is recoverable with a simple extraction using an organic solvent and reusable for at least for 5 cycles without any losses of its activity.
Metal–organic framework of amine-MIL-53(Al) as active and reusable liquid-phase reaction inductor for multicomponent condensation of Ugi-type reactions
Rostamnia, Sadegh,Jafari, Maryam
, (2017/03/24)
Metal–organic framework of NH2-MIL-53(Al), with coordinative unsaturated aluminium sites, has been shown to be active in the Groebke–Blackburn–Bienaymé multicomponent coupling reaction based on Ugi-type amine and aldehyde condensation over isocyanide and then a cyclization process. Interestingly this reaction occurred under solvent-free conditions with high yield, in which the NH2-MIL-53(Al) could be recovered and reused for five reaction cycles, giving a total turnover number of 455.
A facile protocol for the synthesis of 3-aminoimidazo-fused heterocycles via the Groebke-Blackburn-Bienayme reaction under catalyst-free and solvent-free conditions
Vidyacharan, Shinde,Shinde, Anand H.,Satpathi, Bishnupada,Sharada, Duddu S.
supporting information, p. 1168 - 1175 (2014/03/21)
A one-pot catalyst, solvent, work-up and column free synthesis of 3-aminoimidazo-fused heterocycles by a three-component reaction of a 2-aminoheterocycle, aldehyde, and isocyanide is presented. This efficient and green protocol has the advantages of environmental friendliness, high yields and operational simplicity.
Three novel sequential reactions for the facile synthesis of a library of bisheterocycles possessing the 3-aminoimidazo[1,2- a ]pyridine core catalyzed by bismuth(III) chloride
Shahrisa, Aziz,Esmati, Somayeh
, p. 595 - 602 (2013/04/10)
Novel, one-pot, two-step, sequential protocols for the synthesis of 1,4-phenylene bisheterocyclic compounds have been developed. Successive sequencing of the Groebke-Blackburn-Bienaymé reaction with Ugi-azide, Hantzsch and Biginelli reactions results in rapid and efficient formation of bisheterocyclic compounds. A simple, fast and high yielding method for the synthesis of 3-aminoimidazo[1,2-a]pyridines catalyzed by bismuth(III) chloride under solvent-free conditions is reported. Bismuth(III) chloride is also an efficient catalyst for the Ugi-azide reaction under solvent free conditions. Georg Thieme Verlag Stuttgart - New York.
Nanomagnetically modified sulfuric acid (γ-Fe2O3@SiO2-OSO3H): An efficient, fast, and reusable green catalyst for the Ugi-like Groebke-Blackburn-Bienaymé three-component reaction under solvent-free conditions
Rostamnia, Sadegh,Lamei, Kamran,Mohammadquli, Mohsen,Sheykhan, Mehdi,Heydari, Akbar
supporting information, p. 5257 - 5260 (2015/08/27)
Superparamagnetic nanoparticles of modified sulfuric acid (γ-Fe2O3@SiO2-OSO3H) represent a straightforward and green catalyst for the rapid synthesis of aminoimidazopyridine skeletons via the Ugi-like Groebke-Blackburn-Bienaymé three-component reaction. The γ-Fe2O3@SiO2-OSO3H catalyst could be recovered and reused in five reaction cycles, giving a total TON = 453. The products were prepared under solvent-free conditions without any additives.
