Synthesis 2020; 52(22): 3485-3491
DOI: 10.1055/s-0040-1706762
paper

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

Svetlana S. Arabadzhi
,
Mikhail N. Zharkov
,
,
Sergei G. Zlotin


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.

Supporting Information



Publication History

Received: 02 June 2020

Accepted after revision: 13 July 2020

Publication Date:
11 August 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
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