Recent advances in synthesis of quinazoline‐2,4(<i>1H,3H</i>)‐diones: Versatile building blocks in <i>N</i>‐heterocyclic compounds

Gheidari, Davood; Mehrdad, Morteza; Maleki, Saloomeh

doi:10.1002/aoc.6631

Cited by 11 publications

(5 citation statements)

References 148 publications

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“…Then, the conditions search for the implementation of the cyclocondensation was performed. Since the occurrence of similar reactions under basic conditions is described in the literature [50,69], we tested several bases and t-BuONa gave the best results. Having chosen the conditions for the cyclocondensation of the intermediate urea 7, we synthesized thienopyrimidine-2,4-diones 8a-f in the overall yield of 35-56% according to the two-stage one-pot procedure (Scheme 7).…”

Section: Resultsmentioning

confidence: 94%

“…Among the quinazoline and thienopyrimidine diones described in the literature, most of the compounds contain a substituent in position 3. The biological significance causes the emergence of a number of methods for the synthesis of 3-substituted quinazoline-2,4diones, including (i) the treatment of 2-aminobenzamides with phosgene, (ii) the reaction of isatoic anhydride with amines or isocyanates, (iii) the condensation of 2-halobenzoates with monoalkylureas, (iv) Baeyer-Villiger oxidation of 4-iminoisatins, (v) the three-component catalytic condensation of 2-haloanilines with CO 2 and isocyanides (Scheme 1) [49,50]. Instead of phosgene, various phosgene surrogates can be used as a carbonylating agent, including phenylisocyanate [51] or Troc-group [52].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 3-(Pyridin-2-yl)quinazolin-2,4(1H,3H)-diones via Annulation of Anthranilic Esters with N-pyridyl Ureas

Baykova

Geyl

Baykov

et al. 2023

IJMS

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A new route for the synthesis of quinazolin-2,4(1H,3H)-diones and thieno [2,3-d]pyrimidine-2,4(1H,3H)-diones substituted by pyridyl/quinolinyl moiety in position 3 has been developed. The proposed method concluded in an annulation of substituted anthranilic esters or 2-aminothiophene-3-carboxylates with 1,1-dimethyl-3-(pyridin-2-yl) ureas. The process consists of the formation of N-aryl-N′-pyridyl ureas followed by their cyclocondensation into the corresponding fused heterocycles. The reaction does not require the use of metal catalysts and proceeds with moderate to good yields (up to 89%). The scope of the method is more than 30 examples, including compounds with both electron-withdrawing and electron-donating groups, as well as diverse functionalities. At the same time, strong electron-acceptor substituents in the pyridine ring of the starting ureas reduce the product yield or even prevent the cyclocondensation step. The reaction can be easily scaled to gram quantities.

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Section: Resultsmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Synthesis of 3-(Pyridin-2-yl)quinazolin-2,4(1H,3H)-diones via Annulation of Anthranilic Esters with N-pyridyl Ureas

Baykova

Geyl

Baykov

et al. 2023

IJMS

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“…H-bonds with other substances and properties such as amphipathy and acid–base make them excellent catalysts in the reaction process. 197,198 IL-based catalysts provide numerous benefits compared with traditional catalysts, such as their high adjustability and recyclability, reduced metal and halogen pollution, and enhanced separation between the catalyst and the product. In addition, IL-based catalytic systems offer a notable advantage in terms of reducing neutralization after the reaction, thereby enhancing their sustainability.…”

Section: Biomedical Aidsmentioning

confidence: 99%

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

Hu,

Xing,

Yue

et al. 2023

Chem. Soc. Rev.

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“…There are several review articles that have been published for the synthesis of quinazoline-2,4(1 H ,3 H )-diones from CO 2 and o -aminobenzonitriles. Gheidari and Mehrdad et al [ 26 ] have reviewed the recent advances in synthesis of quinazoline-2,4(1 H ,3 H )-diones. Soleimani-Amiri et al [ 27 ] and Zhu et al [ 28 ] have reported the mechanisms and reaction conditions of CO 2 with o -aminobenzonitrile for the synthesis of quinazoline-2,4-dione.…”

Section: Introductionmentioning

confidence: 99%

Tuning Ionic Liquid-Based Catalysts for CO2 Conversion into Quinazoline-2,4(1H,3H)-diones

Zhang

et al. 2023

Molecules

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Carbon capture and storage (CCS) and carbon capture and utilization (CCU) are two kinds of strategies to reduce the CO2 concentration in the atmosphere, which is emitted from the burning of fossil fuels and leads to the greenhouse effect. With the unique properties of ionic liquids (ILs), such as low vapor pressures, tunable structures, high solubilities, and high thermal and chemical stabilities, they could be used as solvents and catalysts for CO2 capture and conversion into value-added chemicals. In this critical review, we mainly focus our attention on the tuning IL-based catalysts for CO2 conversion into quinazoline-2,4(1H,3H)-diones from o-aminobenzonitriles during this decade (2012~2022). Due to the importance of basicity and nucleophilicity of catalysts, kinds of ILs with basic anions such as [OH], carboxylates, aprotic heterocyclic anions, etc., for conversion CO2 and o-aminobenzonitriles into quinazoline-2,4(1H,3H)-diones via different catalytic mechanisms, including amino preferential activation, CO2 preferential activation, and simultaneous amino and CO2 activation, are investigated systematically. Finally, future directions and prospects for CO2 conversion by IL-based catalysts are outlined. This review is benefit for academic researchers to obtain an overall understanding of the synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and o-aminobenzonitriles by IL-based catalysts. This work will also open a door to develop novel IL-based catalysts for the conversion of other acid gases such as SO2 and H2S.

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Recent advances in synthesis of quinazoline‐2,4(1H,3H)‐diones: Versatile building blocks in N‐heterocyclic compounds

Abstract: Quinazoline-2,4(1H,3H)-dione is a significant class of N-fused heterocyclic with a wide range of biological functions, including anti-HIV, anticancer,

Cited by 11 publications

References 148 publications

Synthesis of 3-(Pyridin-2-yl)quinazolin-2,4(1H,3H)-diones via Annulation of Anthranilic Esters with N-pyridyl Ureas

Synthesis of 3-(Pyridin-2-yl)quinazolin-2,4(1H,3H)-diones via Annulation of Anthranilic Esters with N-pyridyl Ureas

Ionic liquids revolutionizing biomedicine: recent advances and emerging opportunities

Tuning Ionic Liquid-Based Catalysts for CO2 Conversion into Quinazoline-2,4(1H,3H)-diones

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