Synthesis of imidazolidin-2-ones employing dialkyl carbonates as an ecofriendly carbonylation source

Badru, Rahul; Singh, Baldev

doi:10.1039/c4ra08048c

Cited by 10 publications

(8 citation statements)

References 46 publications

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“…27 The conventional approach to cyclic ureas involves carbonylation of variously substituted diamines with phosgene. 28,29 Much effort has been made to replace phosgene by its less toxic analogues, such as dialkyl carbonates, 30,31 triphosgene, [32][33][34] 1,1′-carbonyldiimidazole, 35,36 urea, 37 and others. Novel approaches to these compounds, such as the direct carbonylation with carbon monoxide 38,39 or [3+2] cycloaddition of isocyanoacetates with nitrones, 40 are still emerging, indicating a growing area of interest.…”

Section: Published As Part Of the Special Topic Recent Advances In Ammentioning

confidence: 99%

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

et al. 2020

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Imidazolidin-2-one and 1,3-benzodiazepin-2-one scaffolds are structural motifs of many biologically active compounds. Herein, we report a highly regioselective acid-catalyzed intramolecular nucleophilic cyclization/intermolecular electrophilic substitution reaction sequence of (2,2-dialkoxyethyl)ureas. The reaction benefits from readily available starting materials, a simple workup procedure, moderate to high yields of target compounds, and provides a convenient entry to previously unknown 4-(het)arylimidazolidinones and 5-(het)arylbenzodiazepinones. The proposed mechanism of the reaction is also discussed.

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Section: Published As Part Of the Special Topic Recent Advances In Ammentioning

confidence: 99%

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

et al. 2020

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“…The FT-IR spectra of γ-Fe 2 O 3 @SiO 2 , Pyridoxal phosphate γ-Fe 2 O 3 @SiO 2 , and Cu (II)-Pyridoxal phosphate complex γ-Fe 2 O 3 @SiO 2 95% ref [7] 2 B(C 6 F 5 ) 3 (3 mol%) Imine,carbonyl compound, TMSCN CH 2 CL 2 , 20°C, 0.75 h 75% ref [8] 3 For instance, FT-IR, XRD, XRF, VSM, SEM microscopy, TEM imaging, EDS, TGA and ICP analysis.…”

Section: Resultsmentioning

confidence: 99%

“…For instance, FT-IR, XRD, XRF, VSM, SEM microscopy, TEM imaging, EDS, TGA and ICP analysis. 95% ref [7] 2 B(C 6 F 5 ) 3 (3 mol%) Imine,carbonyl compound, TMSCN CH 2 CL 2 , 20°C, 0.75 h 75% ref [8] 3…”

Section: Resultsmentioning

confidence: 99%

Copper‐vitamin B₆ coated on maghemite nanoparticles: A new convenient dual catalysis system to synthesize α‐aminonitriles from benzyl alcohols

Esfandiary

Nakisa

Radfar

et al. 2018

Applied Organom Chemis

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A novel and effective dual catalysis system, copper combined with pyridoxal phosphate, which is anchored in maghemite nanoparticles were designed and applied to synthesize α-aminonitriles from benzyl alcohols. This catalytic system has the potential ability to perform oxidation reactions and subsequently synthesize alpha-amino nitrile in a reaction environment. Thus, the purpose of this paper is introducing a heterogeneous, sustainable and recyclable catalytic system to perform reactions that require a transition metal catalyst and organocatalyst continuously to achieve a target molecule. The catalysis system is examined and investigated with seven useful analyses such as FT-IR, TGA, VSM, SEM, TEM, XRD, and ICP.

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“…In total syntheses of natural products, the application of α‐aminonitriles is a convenient method to selectively transform the available amine function first and after subsequent reduction of the nitrile function, producing a 1,2‐diamine with a second amino group for further modification. The main challenge here is to overcome the reductive decyanation as a competing side reaction, which is the reason why catalytic hydrogenation of α‐aminonitriles over Pd, Rh or Ni under high hydrogen pressure or the use of lithium aluminium hydride often proved insufficient in this context. Instead, low pressure hydrogenations of N ‐unsubstituted α‐aminonitriles in alcoholic HCl over PtO 2 is often the method of choice.…”

Section: α‐Aminonitriles As Key Intermediates In Natural Product Syntmentioning

confidence: 99%

‐Aminonitriles: From Sustainable Preparation to Applications in Natural Product Synthesis

Grundke

Vierengel

Opatz

2020

The Chemical Record

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Due to their numerous reactivity modes, α‐aminonitriles represent versatile and valuable building blocks in organic total synthesis. Since their discovery by Adolph Strecker in 1850, this compound class has seen a wide dissemination in synthetic applications from laboratory to million‐ton industrial scale and was extensively used in the syntheses of various classes of natural products. As these compounds provide a multitude of reactivity options, we feel that a broad overview of their multiple reaction modes may reveal less familiar opportunities for successful total synthesis planning. This personal account article will thus focus on α‐aminonitriles used as key intermediates in selected natural product synthesis sequences which have been reported in the two decades since Enders’ and Shilvock's seminal review. Natural α‐aminonitriles will also briefly be treated.

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Synthesis of imidazolidin-2-ones employing dialkyl carbonates as an ecofriendly carbonylation source

Cited by 10 publications

References 46 publications

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

Copper‐vitamin B₆ coated on maghemite nanoparticles: A new convenient dual catalysis system to synthesize α‐aminonitriles from benzyl alcohols

‐Aminonitriles: From Sustainable Preparation to Applications in Natural Product Synthesis

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Synthesis of imidazolidin-2-ones employing dialkyl carbonates as an ecofriendly carbonylation source

Cited by 10 publications

References 46 publications

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

Nucleophilic Cyclization/Electrophilic Substitution of (2,2-Dialkoxyethyl)ureas: Highly Regioselective Access to Novel 4-(Het)arylimidazolidinones and Benzo[d][1,3]diazepinones

Copper‐vitamin B6 coated on maghemite nanoparticles: A new convenient dual catalysis system to synthesize α‐aminonitriles from benzyl alcohols

‐Aminonitriles: From Sustainable Preparation to Applications in Natural Product Synthesis

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Copper‐vitamin B₆ coated on maghemite nanoparticles: A new convenient dual catalysis system to synthesize α‐aminonitriles from benzyl alcohols