Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles in water without any catalyst

Transformation of carbon dioxide (CO 2 ) into valuable chemicals is an interesting topic in green chemistry. Hydrogenation of CO 2 to methyl formate (MF) in the presence of methanol is an important reaction. In this work, Au nanocatalysts immobilized on different supports were prepared and characterized by X-ray diffraction (XRD), transmission electron microscope (TEM) and X-ray photoelectron spectrometer (XPS). The catalytic performances of the catalysts for the reaction were studied. It was demonstrated that the Au/ZrO 2 , Au/CeO 2 and Au/TiO 2 were very active and selective for the reaction in the absence of any basic additives. The Au/ZrO 2 was more active than Au/CeO 2 and Au/TiO 2 if the sizes of Au particles on the supports were similar. Moreover, for the Au/ZrO 2 catalysts, Au particles with smaller size had higher activity. The possible mechanism of the catalytic reaction was proposed.

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“…38 In a typical experiment, 1.0 g methanol, desired amount of catalyst was added into the reactor. The air in the reactor was replaced by H 2 .…”

Section: Reactionmentioning

confidence: 99%

Highly efficient hydrogenation of carbon dioxide to methyl formate over supported gold catalysts

Zhang

Zhu

et al. 2015

Green Chem.

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“…Beside the formation of organic carbonates and products derived from reductive couplings, the formation of quinazoline−2,4(1H,3H)−diones (see Figure 1 The use of water as a medium has been proposed for the non-catalytic formation of quinazoline−2,4(1H,3H)−diones. 155 In this latter case, the crucial role of the formation of H 2 CO 3 acting as an intermediate was proposed, though higher reaction temperatures/pressures were required and relative longer reaction times were needed for high substrate conversion.…”

Section: Other Reactionsmentioning

confidence: 99%

Sustainable conversion of carbon dioxide: the advent of organocatalysis

2015

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The conversion of carbon dioxide (CO 2 ), an abundant renewable carbon reagent, into chemicals of academic and industrial interest is of imminent importance to create a higher degree of sustainability in chemical processing and production. Recent progress in this field is characterised by a plethora of organic molecules able to mediate the conversion of suitable substrates in the presence of CO 2 into a variety of value-added commodities with advantageous features combining cost-effectiveness, metalfree transformations and general substrate activation profiles. In this review, the latest developments are discussed in the field of CO 2 catalysis with a focus on organo-mediated conversions and their increasing importance as to serve as practicable alternatives for metal-based processes. Also a critical assessment of the state-of-the-art is presented with attention on those features that need further attention to lift the usefulness of organocatalysis in the production of organic molecules of potential commercial interest.

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“…Most of the reported methods are about the synthesis of quinazoline-4-ones [10][11][12][13][14][15] and quinazoline-2,4-(1H,3H)-diones. [16][17][18][19] Only a two-step reaction has been reported for the synthesis of quinazoline-5-ones 8 although octahydroquinazoline-5-ones, for example III in 3…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of a Series of Novel Octahydroquinazoline-5-ones via a Simple on-Water Urea-Catalyzed Chemoselective Five-Component Reaction

et al. 2016

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Multicomponent reactions (MCRs) have become a powerful tool for drug discovery and development owing to their advantages of fast and efficient construction of a large library of products with complexity and diversity. However, conventional MCRs usually proceed in environmentally unfriendly organic solvents rather than in water, a green solvent used by nature for biological chemistry. Herein, a simple and efficient on-water urea-catalyzed chemoselective five-component reaction (5CR) has been developed for the synthesis of a series of novel octahydroquinazoline-5-ones (6), the derivatives of quinazolinones possessing diverse biological activities. The molecular structure of 6{1,1,12} has been confirmed by single-crystal X-ray diffraction. The 5CR can proceed at room temperature under normal atmospheric pressure in good yields and afford a large library of octahydroquinazoline-5-ones with various aromatic and aliphatic substituents at N-1, C-2, and N-3. In addition, a green method has been developed for the synthesis of enaminones, important intermediates in the 5CR and in synthetic chemistry.

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Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles in water without any catalyst

Cited by 88 publications

References 68 publications

Highly efficient hydrogenation of carbon dioxide to methyl formate over supported gold catalysts

Highly efficient hydrogenation of carbon dioxide to methyl formate over supported gold catalysts

Sustainable conversion of carbon dioxide: the advent of organocatalysis

Efficient Synthesis of a Series of Novel Octahydroquinazoline-5-ones via a Simple on-Water Urea-Catalyzed Chemoselective Five-Component Reaction

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