Heterogeneous base catalyzed synthesis of 2-oxazolidinones/2-imidiazolidinones via transesterification of ethylene carbonate with β-aminoalcohols/1,2-diamines

Jagtap, Sachin R.; Patil, Yogesh P.; Fujita, Shin‐ichiro; Arai, Masahiko; Bhanage, Bhalchandra M.

doi:10.1016/j.apcata.2008.02.035

Cited by 32 publications

(21 citation statements)

References 31 publications

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“…Hence, the use of a solid base catalyst is desirable from the viewpoint of economy and green chemistry. Recently, our group reported the synthesis of 2-oxazolidinones and 2-imidiazolidinones via transamination of cyclic carbonates with β-aminoalcohols/1,2-diamines using heterogeneous base catalysts such as basic metal oxides for the first time [201] (Scheme 13).…”

Section: Synthesis Of 2-oxazolidinones/2-imidiazolidinones Via Transementioning

confidence: 99%

Carbon dioxide: a renewable feedstock for the synthesis of fine and bulk chemicals

Patil

Tambade

Jagtap

et al. 2009

Front. Chem. Eng. China

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The syntheses of carbon dioxide (CO 2 ) based industrially important chemicals have gained considerable interest in view of the sustainable chemistry and "green chemistry" concepts. In this review, recent developments in the chemical fixation of CO 2 to valuable chemicals are discussed. The synthesis of five-member cyclic carbonates via, cycloaddition of CO 2 to epoxides is one of the promising reactions replacing the existing poisonous phosgene-based synthetic route. This review focuses on the synthesis of cyclic carbonates, vinyl carbamates, and quinazoline-2,4(1H,3H)-diones via reaction of CO 2 and epoxide, amines/phenyl acetylene, 2-aminobenzinitrile and other chemicals. Direct synthesis of dimethyl carbonate, 1,3-disubstituted urea and 2-oxazolidinones/2-imidazolidinones have limitations at present because of the reaction equilibrium and chemical inertness of CO 2 . The preferred alternatives for their synthesis like transesterification of ethylene carbonate with methanol, transamination of ethylene carbonate with primary amine and transamination reaction of ethylene carbonate with diamines/β-aminoalcohols are discussed. These methodologies offer marked improvements for greener chemical fixation of CO 2 in to industrially important chemicals.

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Section: Synthesis Of 2-oxazolidinones/2-imidiazolidinones Via Transementioning

confidence: 99%

Carbon dioxide: a renewable feedstock for the synthesis of fine and bulk chemicals

Patil

Tambade

Jagtap

et al. 2009

Front. Chem. Eng. China

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“…5-Hydroxymethyloxazolidin-2-one: 13 Method c: Glycerol carbonate (2.5 g, 21.4 mmol) and powdered urea (1.28 g, 21.3 mmol) were placed in a reactor connected to a vacuum system for ammonia and carbon dioxide removal (20 Pa). The mixture was heated at 408 K under stirring for 15 h. At the end of the reaction, the oil obtained was dissolved in the minimum amount of methanol and purified by column chromatography (silica gel 0.06-0.2 mm) with n-hexane/ethyl acetate = 1:1 v/v as the eluent.…”

Section: Reaction Of Glycerol Carbonate and Urea To Afford 2-oxazolidmentioning

confidence: 99%

“…Alternatively, 2-oxazolidinones can be synthesized from aziridines and carbon dioxide [10] or by treating cyclic carbonates with 1,2-amino alcohol. [11][12][13] All such routes are affected by drawbacks such as 1) the formation of polymers that generate a low yield of the target product, 2) unfavorable reaction conditions (high pressure, high temperature), and 3) high costs.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Synthesis of Hydroxymethyl‐2‐oxazolidinones from Glycerol or Glycerol Carbonate and Urea

et al. 2012

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Oxazolidinones have been synthesized by reacting glycerol carbonate or glycerol with urea in the presence of γ-Zr phosphate as a catalyst. The conversion yield of the polyol or its carbonate depends on the temperature. Below 408 K the selectivity is 100 % with a conversion of up to 25 %, whereas increasing the temperature means that conversion yield grows, but the selectivity decreases, which makes the separation process more difficult. Starting from glycerol carbonate, two isomers, 6 and 6', are formed with a quasi 1:1 molar ratio because urea can attack the carbonate moiety on both sides of the carboxylic CO moiety. From glycerol the formation of the 6' isomer is preferred: the ratio of 6'/6 is close to 7. The oxazolidinones formed act as templates because they interact through hydrogen bonding with glycerol. The intensity of the interaction depends on the 6 or 6' isomer: DFT calculations showed that the energy was 22.6 kcal mol(-1) for 6-oxazolidinone and 25.7 kcal mol(-1) for 6'-oxazolidinone.

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“…[21][22][23] Conventionally,2 -imidazolidinones and other cyclic ureas are synthesized by the reaction of diamines with several reagents such as carbonyldiimidazole, [24] trichloromethyl chloroformate, [25] organic carbonates, [26,27] dithiocarbonate, [28] carbonyl selenide, [29,30] and carbon monoxide (Scheme 1). [21][22][23] Conventionally,2 -imidazolidinones and other cyclic ureas are synthesized by the reaction of diamines with several reagents such as carbonyldiimidazole, [24] trichloromethyl chloroformate, [25] organic carbonates, [26,27] dithiocarbonate, [28] carbonyl selenide, [29,30] and carbon monoxide (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Imidazolidinones and Imidazolidine‐2,4‐diones as Antiviral Agents

Swain

Mohanty

2019

ChemMedChem

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Imidazolidinones and imidazolidine‐2,4‐diones are important classes of heterocyclic compounds that possess potent activities against several viruses such as dengue virus, enterovirus, hepatitis C virus (HCV), and human immunodeficiency virus (HIV). The first imidazolidinone derivative as an anti‐HIV agent was reported in 1996. Imidazolidinones inhibit HIV aspartic protease activity, and also act as CCR5 co‐receptor antagonists. Significant effort has been devoted to the design of various imidazolidinone analogues that are active against drug‐resistant HIV strains, with fewer side effects. Different scaffolds have been designed through both rational drug design strategies and computer‐aided drug design. Imidazolidinones have been found to be potent against HIV, and preclinical studies are currently in progress. There are some reports of imidazolidinones as having both anti‐HCV and anti‐dengue virus activity, and more research has yet to be done along these lines. These compounds inhibit NS3 serine protease of HCV, and NS2B‐NS3 protease of dengue virus. Pyridyl‐imidazolidinones possess very specific and potent activity against human enterovirus 71 (EV71) by targeting the EV71 capsid protein VP1, and inhibiting viral adsorption and/or viral RNA uncoating.

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Heterogeneous base catalyzed synthesis of 2-oxazolidinones/2-imidiazolidinones via transesterification of ethylene carbonate with β-aminoalcohols/1,2-diamines

Cited by 32 publications

References 31 publications

Carbon dioxide: a renewable feedstock for the synthesis of fine and bulk chemicals

Carbon dioxide: a renewable feedstock for the synthesis of fine and bulk chemicals

Catalytic Synthesis of Hydroxymethyl‐2‐oxazolidinones from Glycerol or Glycerol Carbonate and Urea

Imidazolidinones and Imidazolidine‐2,4‐diones as Antiviral Agents

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