Alcohol amine-catalyzed CO2 conversion for the synthesis of quinazoline-2,4-(1H,3H)-dione in water

Sheng, Zhizheng; Huang, Mei; Xue, Teng; Xia, Fei; Wu, Haihong

doi:10.1039/d0ra06439d

Cited by 11 publications

(4 citation statements)

References 39 publications

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“…After five cycles there was no significant loss of catalytic activity. DEA played an important role in the activation of reactants in addition to the activation of 2-aminobenzonitrile and CO 2 …”

Section: Current Status Of Co2 Fixation To Form Quinazolinementioning

confidence: 99%

“…DEA played an important role in the activation of reactants in addition to the activation of 2-aminobenzonitrile and CO 2 . 251 In 2002, Mizuno and his group synthesized 1H-quinazoline-2,4-diones via CO 2 catalyzed by DBU. The influence of different bases such as DBU, DBN, Dabco, K 2 CO 3 , Et 3 N, NaOH, NaHCO 3 and pyridine showed a maximum yield of 98% by DBU.…”

Section: Various Catalysts Such As [Dabco-pdo][cl] Ps-dmap][cl] [Dabc...mentioning

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 To Form Quinazolinementioning

confidence: 99%

Section: Various Catalysts Such As [Dabco-pdo][cl] Ps-dmap][cl] [Dabc...mentioning

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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show abstract

“…The selection of the corresponding ethanolamine catalysts was based on their known environmental behaviour, i.e., ready biodegradation and low bioaccumulation potential, cost-effectiveness, as well as on their extensive application in industry and common consumer products. [53][54][55] The reaction progress was monitored using thin-layer chromatography. The optimal time for conversion of starting material in all cases was 3 h. It is worth pointing out, that formation of the product was observed in all tested reactions.…”

Section: Synthesis Of Pyrazolone Derivativesmentioning

confidence: 99%

Pyrazolone-type compounds: synthesis andin silicoassessment of antiviral potential against key viral proteins of SARS-CoV-2

et al. 2022

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“…Therefore, several alternative methods have been developed to overcome these disadvantages. One such synthetic method involves the carbonylation of 2-aminobenzonitrile with carbon dioxide − and transition metal-free catalytic reactions of 2-aminobenzamides with different sources such as carbon monoxide and (Boc) 2 . Another method includes an earth metal-catalyzed (Lanthanum) reaction using phenyl isocyanate (Scheme b) .…”

Section: Introductionmentioning

confidence: 99%

Metal-Free N–H/C–H Carbonylation by Phenyl Isocyanate: Divergent Synthesis of Six-Membered N-Heterocycles

et al. 2022

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We disclose a method using phenyl isocyanate to synthesize carbonyl-containing N-heterocycles. The metal-free novel approach for both N–H and C–H carbonylation processes was successfully refined, delivering a range of synthetically valuable derivatives of quinazoline-2,4(1H,3H)-dione, 2H-benzo[e] [1,2,4] thiadiazin-3(4H)-one 1,1-dioxide, and pyrrolo[1,2-a] quinoxalin-4(5H)-one. The protocol features broad substrates with diverse reactions suitable for excellent yields, mild conditions, and good functional group compatibility. Moreover, the applicability of the reaction was characterized by gram-scale synthesis and synthetic transformations for drug molecules.

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Alcohol amine-catalyzed CO₂ conversion for the synthesis of quinazoline-2,4-(1H,3H)-dione in water

Abstract: Commercial DEA is proposed for efficiently promoting the cyclization of CO2 and 2-aminobenzonitrile to quinazoline-2,4(1H,3H)-dione (up to 94% yield) while water acts as the solvent and co-catalyst.

Cited by 11 publications

References 39 publications

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole

Pyrazolone-type compounds: synthesis andin silicoassessment of antiviral potential against key viral proteins of SARS-CoV-2

Metal-Free N–H/C–H Carbonylation by Phenyl Isocyanate: Divergent Synthesis of Six-Membered N-Heterocycles

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Alcohol amine-catalyzed CO2 conversion for the synthesis of quinazoline-2,4-(1H,3H)-dione in water

Abstract: Commercial DEA is proposed for efficiently promoting the cyclization of CO2 and 2-aminobenzonitrile to quinazoline-2,4(1H,3H)-dione (up to 94% yield) while water acts as the solvent and co-catalyst.

Cited by 11 publications

References 39 publications

Recent Advances in the Fixation of CO2 into Quinazoline and Benzimidazole

Recent Advances in the Fixation of CO2 into Quinazoline and Benzimidazole

Pyrazolone-type compounds: synthesis andin silicoassessment of antiviral potential against key viral proteins of SARS-CoV-2

Metal-Free N–H/C–H Carbonylation by Phenyl Isocyanate: Divergent Synthesis of Six-Membered N-Heterocycles

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Product

Resources

About

Alcohol amine-catalyzed CO₂ conversion for the synthesis of quinazoline-2,4-(1H,3H)-dione in water

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole

Recent Advances in the Fixation of CO₂ into Quinazoline and Benzimidazole