Trapping carbamates of α-Amino acids: One-Pot and catalyst-free synthesis of 5-Aryl-2-Oxazolidinonyl derivatives

Bresciani, Giulio; Zacchini, Stefano; Famlonga, Luca; Pampaloni, Guido; Marchetti, Fabio

doi:10.1016/j.jcou.2021.101495

Cited by 3 publications

(2 citation statements)

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“…In the framework of our interest in the chemistry of carbamates [57][58][59][60], we recently developed a catalystfree method to access 5-aryl-2-oxazolidinones directly from aziridine precursors, amines and carbon dioxide, working at ambient temperature and pressure [61]. This strategy allows for unprecedented access to molecules with uncommon substituents on the nitrogen ring, including the -NH 2 group and the skeleton of several natural α-amino-acids [62].…”

Section: Synthesis and Spectroscopic Characterizationmentioning

confidence: 99%

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Adding Diversity to Diiron Aminocarbyne Complexes with Amine Ligands

et al. 2023

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The reactions of the diiron aminocarbyne complexes [Fe2Cp2(NCMe)(CO)(μ-CO){μ-CN(Me)(R)}]CF3SO3 (R = Me, 1aNCMe; R = Cy, 1bNCMe), freshly prepared from the tricarbonyl precursors 1a–b, with primary amines containing an additional function (i.e., alcohol or ether) proceeded with the replacement of the labile acetonitrile ligand and formation of [Fe2Cp2(NH2CH2CH2OR’)(CO)(μ-CO){μ-CN(Me)(R)}]CF3SO3 (R = Me, R’ = H, 2a; R = Cy, R’ = H, 2b; R = Cy, R’ = Me, 2c) in 81–95% yields. The diiron-oxazolidinone conjugate [Fe2Cp2(NH2OX)(CO)(μ-CO){μ-CN(Me)2}]CF3SO3, 3, was prepared from 1a, 3-(2-aminoethyl)-5-phenyloxazolidin-2-one (NH2OX) and Me3NO, and finally isolated in 96% yield. In contrast, the one pot reactions of 1a-b with NHEt2 in the presence of Me3NO gave the unstable [Fe2Cp2(NHEt2)(CO)(μ-CO){μ-CN(Me)(R)}]CF3SO3 (R = Me, 4a; R = Cy, 4b) as unclean products. All diiron complexes were characterized by analytical and spectroscopic techniques; moreover, the behavior of 2a–c and 3 in aqueous media was ascertained.

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Section: Synthesis and Spectroscopic Characterizationmentioning

confidence: 99%

“…Inorganics 2023, 11, x FOR PEER REVIEW 4 and the skeleton of several natural α-amino-acids [62]. We selected 3-(2-aminoethy phenyloxazolidin-2-one (NH2 OX ) as an appropriate amine reagent towards d aminocarbyne acetonitrile complexes (Scheme 4).…”

Section: Synthesis and Spectroscopic Characterizationmentioning

confidence: 99%

Adding Diversity to Diiron Aminocarbyne Complexes with Amine Ligands

et al. 2023

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The Contribution of CIRCC Partners to the Birth and Growth of CO₂ Chemistry

Aresta

2022

Eur J Inorg Chem

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This paper tells the recent history of CO2 chemistry through the contributions from members of CIRCC to its birth and growth. Starting with the first transition metal complex bearing CO2 as a ligand synthesized in 1975 by the Aresta Group in Bari, the mode of bonding and the reactivity of coordinated CO2 are discussed. The early applications in chemo‐thermal, electrolytic, and biotechnological processes, and the use of SC‐CO2 as solvent and reagent are fields in which CIRCC partners have made pioneering contributions and continue to provide essential inputs. The paper is closed by highlighting key issues and challenges at stake, from capture to large‐scale conversion, investment infrastructure, progressive policies and standardized regulations needed to advocate carbon recycling as a pillar of future innovation in energy and chemical industries. CIRCC has been the nest of modern CO2 chemistry and the place where CO2 has always been considered a “resource” rather than a “waste”.

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