Convenient synthesis of novel C2-symmetric bisoxazolidine derivatives containing a sulfonamide moiety

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2025-06-18 DOI:10.1080/00397911.2025.2505905

L. Boughani (Conceptualization Investigation Methodology Validation Visualization Writing – original draft Writing – review & editing) , D. Bouchouk (Methodology Visualization) , T. Abbaz (Methodology Visualization) , A. Bendjeddou (Methodology Visualization) , Z. Regainia (Conceptualization Methodology Supervision)

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引用次数: 0

Abstract

A new series of C₂-symmetric bisoxazolidines containing a sulfonamide moiety has been prepared. The synthesis started by reducing the bisaminoester sulfonamides derived from natural amino acids by lithium aluminum hydride (LiAlH₄). The bisaminoalcohol sulfonamides resulting from the reduction react with aliphatic and aromatic aldehydes in an acidic medium to form heterocyclic compounds. The obtained N,N’-sulfonyl-bisoxazolidines are isolated in good yields. Bisoxazolidines derived from paraformaldehyde crystallize in ether, yielding their bridged [4.4.1] bicyclic isomers. The structures of synthesized compounds have been explored and validated using standard spectroscopic techniques, such as NMR, IR, and mass spectrometry.

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含磺酰胺部分的新型c2对称双恶唑烷衍生物的便捷合成

制备了一系列新的含有磺胺部分的c2对称双恶唑烷。首先用氢化铝锂（LiAlH4）还原天然氨基酸衍生的双氨基酯磺酰胺。由还原产生的双氨基醇磺酰胺在酸性介质中与脂肪醛和芳香醛反应形成杂环化合物。所得到的N，N ' -磺酰基双恶唑烷的分离率很高。多聚甲醛衍生的双恶唑烷在醚中结晶，生成桥接[4.4.1]双环异构体。合成化合物的结构已被探索和验证使用标准的光谱技术，如核磁共振，红外和质谱。

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.