Direct assembly of 2-oxazolidinones by chemical fixation of carbon dioxide

Teemu Niemi; Jesus E. Perea-Buceta; Israel Fernández; Sami Alakurtti; Erika Rantala; Timo Repo

doi:10.1002/chem.201402368

Direct assembly of 2-oxazolidinones by chemical fixation of carbon dioxide

Teemu Niemi, Jesus E. Perea-Buceta, Israel Fernández, Sami Alakurtti, Erika Rantala, Timo Repo^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Scientific › peer-review

25 Citations (Scopus)

Abstract

The reaction of β- and γ-haloamines with carbon dioxide to give pharmaceutically relevant 2-oxazolidinones and 1,3-dioxazin-2-ones, was found to proceed efficiently in the presence of a base and in the absence of catalyst. After optimization of reaction conditions, the system was successfully expanded to a variety of haloamines, even at multigram scale. The reaction was further studied in silico by DFT calculations.

Original language	English
Pages (from-to)	8867-8871
Journal	Chemistry - A European Journal
Volume	20
Issue number	29
DOIs	https://doi.org/10.1002/chem.201402368
Publication status	Published - 2014
MoE publication type	A1 Journal article-refereed

Keywords

2-oxazolidones
antibiotics
carbon dioxide activation
carbon dioxide fixation
density functional calculations

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10.1002/chem.201402368

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title = "Direct assembly of 2-oxazolidinones by chemical fixation of carbon dioxide",

abstract = "The reaction of β- and γ-haloamines with carbon dioxide to give pharmaceutically relevant 2-oxazolidinones and 1,3-dioxazin-2-ones, was found to proceed efficiently in the presence of a base and in the absence of catalyst. After optimization of reaction conditions, the system was successfully expanded to a variety of haloamines, even at multigram scale. The reaction was further studied in silico by DFT calculations.",

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AU - Niemi, Teemu

AU - Perea-Buceta, Jesus E.

AU - Fernández, Israel

AU - Alakurtti, Sami

AU - Rantala, Erika

AU - Repo, Timo

PY - 2014

Y1 - 2014

N2 - The reaction of β- and γ-haloamines with carbon dioxide to give pharmaceutically relevant 2-oxazolidinones and 1,3-dioxazin-2-ones, was found to proceed efficiently in the presence of a base and in the absence of catalyst. After optimization of reaction conditions, the system was successfully expanded to a variety of haloamines, even at multigram scale. The reaction was further studied in silico by DFT calculations.

AB - The reaction of β- and γ-haloamines with carbon dioxide to give pharmaceutically relevant 2-oxazolidinones and 1,3-dioxazin-2-ones, was found to proceed efficiently in the presence of a base and in the absence of catalyst. After optimization of reaction conditions, the system was successfully expanded to a variety of haloamines, even at multigram scale. The reaction was further studied in silico by DFT calculations.

KW - 2-oxazolidones

KW - antibiotics

KW - carbon dioxide activation

KW - carbon dioxide fixation

KW - density functional calculations

U2 - 10.1002/chem.201402368

DO - 10.1002/chem.201402368

M3 - Article

SN - 0947-6539

VL - 20

SP - 8867

EP - 8871

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

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ER -

Direct assembly of 2-oxazolidinones by chemical fixation of carbon dioxide

Abstract

Keywords

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