Aminoguanidine-Catalyzed Reductive Cyclization of o-Phenylenediamines with CO<sub>2</sub> in the Presence of Triethoxysilane

Sun, Yi; Gao, Ke

doi:10.1021/acs.joc.3c00026

Cited by 6 publications

(3 citation statements)

References 36 publications

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“…It was found that the aminoguanidine hydrochloride salt catalyst provided a 97% yield toward benzimidazole in the presence (EtO) 3 SiH under atmospheric CO 2 pressure at 100 °C for 6 h (Table , entry 5). Further substrate scope was also studied, which gave an efficient yield . Liu and co-workers synthesized benzimidazole via CO 2 fixation catalyzed by B(C6F5) 3 .…”

Section: Current Status Of Co2 Fixation For the Synthesis Of Benzimid...mentioning

confidence: 99%

“…Further substrate scope was also studied, which gave an efficient yield. 217 Liu and co-workers synthesized benzimidazole via CO 2 fixation catalyzed by B(C6F5) 3 . With a catalyst loading of 5 mol % in the presence of the solvent (EtO) 3 SiH and DMF as a base at 120 °C and a CO 2 pressure of 1 bar for 24 h, an excellent yield of 99% was achieved with a conversion of >99% (Table 1, entry 6).…”

Section: Introductionmentioning

confidence: 99%

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Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole

Rajanna,

Srinivasappa,

Sudhakaran

et al. 2024

Energy Fuels

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CO 2 is an important component of the atmosphere that helps in balancing the Earth's atmospheric temperature and channelizes the food cycles. However, an increase or decrease in the concentration will severely affect the climate. Particularly, the rise in CO 2 levels has immensely contributed to global warming, resulting in elevated atmospheric temperature, altered precipitation patterns, glacier melting, and subsequent rises in sea levels, impacting human well-being. In response, researchers are exploring strategies to capture and convert CO 2 into valuable products, such as methanol, formic acid, and organic compounds. Particularly, the synthesis of organic compounds using CO 2 , like benzimidazole and quinazolines, has a high impact. Benzimidazole, widely used in medicinal chemistry for treating cancer and stomach ulcers, also exhibits antiviral and antifungal properties. Quinazoline derivatives, essential in drugs like prazosin and doxazosin, have applications in treating post-traumatic stress disorder and Alzheimer's disease. These compounds were synthesized mainly using environmentally harmful synthons such as phosgene and potassium cyanide. To address both environmental and health concerns, researchers are delving into the chemical fixation of CO 2 for sustainable and green production. Catalysis emerges as a key principle in green chemistry, with catalysts reducing activation energy and facilitating sustainable processes. This review discusses recent state of the art on the development of various catalysts for conversion of CO 2 to quinazoline and benzimidazole, through various homogeneous and heterogeneous catalysts. Notably, while homogeneous catalysts lack industrial recyclability, heterogeneous catalysts show promise for large-scale implementation. This comprehensive review discusses the mechanistic aspects with DFT studies in understanding the catalysts better. Toward the end, it gives the future scope and aspects on this subject.

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Section: Current Status Of Co2 Fixation For the Synthesis Of Benzimid...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole

Rajanna,

Srinivasappa,

Sudhakaran

et al. 2024

Energy Fuels

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“…Heterocyclic compounds play an essential role in the development of contemporary materials science, the pharmaceutical industry, synthetic organic chemistry, and so on. , For example, benzimidazoles and their derivatives emerged as a very important class of N-heterocyclic systems due to their remarkable biological characteristics of anticonvulsant, anti-inflammatory, antiallergic, antipyretic, antidepressive, and others. − It has been also found in several common drugs, such as omeprazole, maribavir, bendamustine, nocodazole, Albendazole, Mebendazole, and so on. − In this sense, the synthesis of benzimidazole is quite important for the current time attributing its increasing applications to the development medicinal field. − However, the synthesis of benzimidazole has faced some problems, such as low yields, more byproducts, harsh reaction conditions, and so on. ,,− Therefore, it is still necessary to develop catalytic systems for the construction of benzimidazole with the advantages of simple operation, catalyst recyclability, and high yield.…”

Section: Introductionmentioning

confidence: 99%

Three Polyoxometalate-Based Ag–Organic Compounds as Heterogeneous Catalysts for the Synthesis of Benzimidazoles

Liu,

Lin,

Ming

et al. 2024

Inorg. Chem.

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Three new POM-based compounds, with formulae [Na 0 . 6 3 Ag 3 (Htba) 2 . 3 7 (tba) 0 . 6 3 (H 2 O) 2 (PMo 1 2 O 4 0 )]•4H 2 O (Ag 3 PMo), [Ag 4 (Htba) 4 (H 2 O) 2 (PMo 12 O 40 )](NO 3 )•H 2 O (Ag 4 PMo), and [Ag 3 (Htba) 2 (tba)(PW 12 O 40 ) 0.5 ](NO 3 ) 0.5 •13H 2 O (Ag 3 PW), were prepared with a 3-(4H-1,2,4-triazol-4-yl)benzoic acid (Htba) ligand, Keggin-type anions ([PMo 12 O 40 ] 3− / [PW 12 O 40 ] 3− ), and a silver ion (Ag + ). The structural features of these compounds are particularly different from the multinuclear subunits, which are [Ag 3 (tba) 3 ] clusters in Ag 3 PMo, [Ag 4 (tba) 3 ] chains in Ag 4 PMo, and [Ag 3 (tba) 3 ] 2 clusters in Ag 3 PW, connected by multidonor atom tba ligands and Ag + ions. Meanwhile, in these compounds, polyanions act as polydentate ligands to link adjacent Ag-tba metal−organic units and expand their spatial dimensions. These compounds, as heterogeneous catalysts, exhibit high stability and excellent catalytic activity to construct benzimidazoles. Ag 3 PMo could efficiently catalyze the condensation of benzene-1,2diamines and benzaldehydes and produce benzimidazoles in good yields. In addition, Ag 3 PMo could be reused up to 7 times and was suitable for gram-scale reactions.

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Five-membered ring systems: With more than 1 N atom

Yet

2024

Progress in Heterocyclic Chemistry

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Aminoguanidine-Catalyzed Reductive Cyclization of o-Phenylenediamines with CO₂ in the Presence of Triethoxysilane

Cited by 6 publications

References 36 publications

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole

Three Polyoxometalate-Based Ag–Organic Compounds as Heterogeneous Catalysts for the Synthesis of Benzimidazoles

Five-membered ring systems: With more than 1 N atom

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Aminoguanidine-Catalyzed Reductive Cyclization of o-Phenylenediamines with CO2 in the Presence of Triethoxysilane

Cited by 6 publications

References 36 publications

Recent Advances in the Fixation of CO2 into Quinazoline and Benzimidazole

Recent Advances in the Fixation of CO2 into Quinazoline and Benzimidazole

Three Polyoxometalate-Based Ag–Organic Compounds as Heterogeneous Catalysts for the Synthesis of Benzimidazoles

Five-membered ring systems: With more than 1 N atom

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Product

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Aminoguanidine-Catalyzed Reductive Cyclization of o-Phenylenediamines with CO₂ in the Presence of Triethoxysilane

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole