The solvent-free and catalyst-free conversion of an aziridine to an oxazolidinone using only carbon dioxide

Phung, Chau; Ulrich, Rani M.; Ibrahim, Mostafa; Tighe, Nathaniel T. G.; Lieberman, Deborah L.; Pinhas, Allan R.

doi:10.1039/c1gc15850c

Cited by 83 publications

(38 citation statements)

References 14 publications

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“…It has also been observed that the insertion of CO 2 in 2-alkyl-Ntosylaziridine is possible to produce oxazolidinone compound without any catalyst, solvent, high temperature, or pressure, when high-speed ball milling has been applied (Scheme 72) [130]. The mechanism of the reaction is shown in Scheme 73.…”

Section: Synthesis Of Oxazolidines Oxazolines and Oxazolesmentioning

confidence: 96%

Ring Expansions of Activated Aziridines and Azetidines

Ghorai

Bhattacharyya

Das

et al. 2015

Topics in Heterocyclic Chemistry

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Facile construction of small and normal-sized, or more precisely, four to seven-membered aza-heterocyclic ring systems is always a challenging yet rewarding task for the synthetic organic chemists. Fortunately, activated aziridines and azetidines provide a direct and convenient access to this coveted molecular architectures through several elegant ring-expansion approaches. This chapter presents some of the illustrative and contemporary examples to demonstrate the synthetic diversity and efficiency of the ring-expansion strategies of activated aziridines and azetidines towards a vast array of small to normal-sized aza-heterocyclic moieties.

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Section: Synthesis Of Oxazolidines Oxazolines and Oxazolesmentioning

confidence: 96%

Ring Expansions of Activated Aziridines and Azetidines

Ghorai

Bhattacharyya

Das

et al. 2015

Topics in Heterocyclic Chemistry

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“…The effect of this isomerization process could almost be fully suppressed under the reaction conditions (0 C) but becomes a significant competitive pathway at room temperature or in the absence of a halide [109,110], organocatalysts such as N-heterocyclic carbenes [111], or recyclable systems based on a polyethylene glycol support containing quaternary NBu 3 Br groups [112] and polymer-supported amino acids [21]. Interestingly, Pinhas et al demonstrated that the coupling of aziridines and CO 2 could also be performed without catalyst using 2-aryl-and 2-alkylaziridines as substrates affording selectively the 5-oxazolidinones in good yields making use of high-speed ball milling as a mechanical stimulus [113]. However, this section focuses on metal-mediated processes; thus, these latter examples fall out of the primary scope of this chapter.…”

Section: Insertion Of Co 2 Into An Aziridine Moietymentioning

confidence: 97%

Metal Complexes Catalyzed Cyclization with CO2

Rintjema

Carrodeguas

Laserna

et al. 2015

Topics in Organometallic Chemistry

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This chapter describes in general terms the catalytic methodology that has been made available for the use of carbon dioxide (CO 2 ) in cyclization reactions that incorporate an intact CO 2 fragment without changing the formal oxidation state of the carbon center. The major focus of this chapter will be on the most successful organometallic/inorganic complexes that have been used as catalyst systems throughout the last decade and the preferred ligand frameworks leading to elevated reactivity and/or selectivity behavior in CO 2 coupling reactions. Attention will be especially given to homogeneous catalyst systems as they have proven to be more versatile in CO 2 conversion catalysis and often have modular characteristics that allow for optimization of structure-activity relationships. The most important reactions that have been studied in the current context are designated CO 2 "addition" reactions to small molecule heterocycles such as epoxides and aziridines, though more recently other coupling partners such as diamines, dialcohols, and amino nitriles have further advanced the use of CO 2 in organic synthesis providing access to a wider range of structures. This chapter will serve to demonstrate the utility of CO 2 as a carbon reagent in the catalytic formation of the most prominent organic structures using cyclization strategies specifically.

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“…43,44 A simple way to synthesize the oxazolidinone ring is by the reaction of an unactivated 2-alkyl or 2-aryl aziridine with carbon dioxide in the absence of any catalyst or solvent under high speed ball milling (Scheme 1.47). 45 When the reaction of 2-aryl substituted aziridine with CO 2 was performed in a conventional way the corresponding oxazolidinone 38 was obtained. However, when the same reaction was performed with an alkyl-substituted aziridine 39, it afforded a mixture of oxazolidinones 40 and 41.…”

Section: Nitrogen-oxygen-containing Heterocyclesmentioning

confidence: 99%