Synthesis of Chiral N-Nitro-oxazolidin-2-ones and O-(β-Nitraminoalkyl) Carbamates in Liquefied 1,1,1,2-Tetrafluoroethane Medium,Synthesis

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Synthesis of Chiral N-Nitro-oxazolidin-2-ones and O-(β-Nitraminoalkyl) Carbamates in Liquefied 1,1,1,2-Tetrafluoroethane Medium
Synthesis ( IF 2.2 ) Pub Date : 2020-08-11 , DOI: 10.1055/s-0040-1706762
Sergei G. Zlotin , Svetlana S. Arabadzhi , Mikhail N. Zharkov , Ilya V. Kuchurov

Abstract

A convenient synthesis of chiral N-nitro-oxazolidin-2-ones by nitration of α-amino acid derived 1,3-oxazolidin-2-ones containing one or two stereogenic centers with dinitrogen pentoxide in liquefied 1,1,1,2-tetrafluoroethane medium has been developed. The obtained N-nitroheterocycles were converted into enantiomerically pure O-(β-nitraminoalkyl) carbamates by treatment with ammonia or amines in the same solvent. The synthesized N-nitro compounds are slightly toxic in vitro to Human Embryonic Kidney 293 (HEK293) cells.

Publication History

Received: 02 June 2020

Accepted after revision: 13 July 2020

Publication Date:
11 August 2020 (online)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

在液化的1,1,1,2-四氟乙烷介质中合成手性N-硝基-恶唑烷-2-酮和O-（β-硝基氨基烷基）氨基甲酸酯

摘要

通过在液化的1,1,1,2-中与五氧化二氮中的一个或两个立体生成中心的α-氨基酸衍生的1,3-恶唑烷-2-酮进行硝化反应，方便地合成手性N-硝基-恶唑烷-2-酮已经开发了四氟乙烷介质。通过在相同溶剂中用氨或胺处理，将获得的N-硝基杂环转化为对映体纯的O-（β-硝胺氨基烷基）氨基甲酸酯。合成的N-硝基化合物在体外对人胚肾293（HEK293）细胞有轻微毒性。