Synthesis of 2-Oxazolidinones by Direct Palladium-Catalyzed Oxidative Carbonylation of 2-Amino-1-alkanols

Gabriele, Bartolo; Salerno, Giuseppe; Brindisi, Donatella; Costa, Mirco; Chiusoli, Gian Paolo

doi:10.1021/ol9913789

Cited by 107 publications

(51 citation statements)

References 9 publications

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“…Carbonylation of diols and aminodiols was also developed in similar conditions [128]. In 2000, Gabriele and co-workers [129,130]. In 2003, they improved this method to be carried out under relatively mild conditions (100 C and 20 atm of a 4:1 mixture of CO and air).…”

Section: Synthesis Of Six-membered Heterocycles Via Oxidative Carbonymentioning

confidence: 99%

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Xing

2015

Topics in Heterocyclic Chemistry

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With the assistance of a proper oxidant, carbonylation of two nucleophiles can take place directly in carbonylation conditions, which is defined as oxidative carbonylation. This process starts with the reaction of nucleophiles with the metal catalyst in oxidation state (M (n + 2) ), followed by insertion of CO and subsequent reductive elimination, providing the carbonylated products and the metal catalyst in reduction state (M (n) ). The oxidant could reoxidize M (n) to M (n + 2) to promote the catalytic cycle. Oxidative carbonylation avoids the difficult oxidative addition of R-X to metal catalyst, so this kind of carbonylation could proceed in mild conditions. What's more is that oxidative carbonylation doesn't need prefunctionalization of substrates. So, it's no wonder that considerable attention has been drawn to construct important carbonylated compounds through oxidative carbonylation. Particularly, much progress in synthesis of carbonylated heterocycles via oxidative carbonylation has been achieved in the past decades. Here, we summarized the main achievements in this area from 1982 to the beginning of 2015.

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Section: Synthesis Of Six-membered Heterocycles Via Oxidative Carbonymentioning

confidence: 99%

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Xing

2015

Topics in Heterocyclic Chemistry

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“…[3] The synthesis of these cyclic carbamates is generally performed by condensation of 1,2-amino alcohols [4] with carbonyl derivatives such as phosgene, [5] triphosgene, [6] isocyanates, [4] chloroformates, [7] ureas, [8] or diethyl carbonate. [9] The catalyzed addition of CO 2 , [10] and the palladium-catalyzed oxidative carbonylation [11] of b-amino alcohols have also been employed. Other methods include the reaction of epoxides with isocyanates, [12] and the reaction of alkenes with N-bromosuccinimide and isocyanates.…”

Section: Introductionmentioning

confidence: 99%

Ring‐Closure Reactions through Intramolecular Displacement of the Phenylselenonyl Group by Nitrogen Nucleophiles: A New Stereospecific Synthesis of N‐Tosyl and N‐Benzoyl‐1,3‐oxazolidin‐2‐ones from β‐Hydroxyalkyl Phenyl Selenides

Tiecco

Testaferri

Temperini

et al. 2004

Chemistry A European J

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A new and convenient method for the stereospecific synthesis of variously substituted 1,3-oxazolidin-2-ones from the easily available beta-hydroxyalkyl phenyl selenides is presented. After transformation into the N-tosyl or N-benzoyl carbamates, the selenides were oxidized to the corresponding selenones. The key step of the process is the ring-closure reaction, which occurs by stereospecific intramolecular nucleophilic substitution of the selenone group by the nitrogen atom of the carbamate. Enantiomerically pure 1,3-oxazolidin-2-one derivatives can be easily prepared by using enantiomerically pure beta-hydroxyalkyl phenyl selenides as starting materials.

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“…2-Imidiazolidinones have recently attracted much attention due to their manifold applications as intermediates for biologically active molecules, such as the HIV protease inhibitors, DMP 323 and DMP 450 [186]. Conventionally 2-imidiazolidinones and 2-oxazolidinones are synthesized by reaction of 1,2-diamines and β-aminoalcohols with several reagents like phosgene [187], urea [188] dialkyl carbonates [189,190] or the mixture CO/O 2 via, oxidative carbonylation [191] (Scheme 12). The synthesis using urea has a major drawback such as the formation of large quantities of polyurea along with the requirement of high temperature [192].…”

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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Synthesis of 2-Oxazolidinones by Direct Palladium-Catalyzed Oxidative Carbonylation of 2-Amino-1-alkanols

Cited by 107 publications

References 9 publications

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Ring‐Closure Reactions through Intramolecular Displacement of the Phenylselenonyl Group by Nitrogen Nucleophiles: A New Stereospecific Synthesis of N‐Tosyl and N‐Benzoyl‐1,3‐oxazolidin‐2‐ones from β‐Hydroxyalkyl Phenyl Selenides

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

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