An Unexpected Formation of Spiro Isoxazoline-Dihydrofurane Compounds from Substituted Ketofurfuryl Alcohols.

IF 4.2 2区化学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Molecules Pub Date : 2024-11-20 DOI:10.3390/molecules29225474

Claire Cuyamendous, Mathieu Yves Laurent, Christine Saluzzo

引用次数: 0

Abstract

Oximation of substituted ketofurfuryl alcohols in the presence of hydroxylamine hydrochloride and pyridine in ethanol as solvent led to a new class of spiro derivatives presenting a 7-methylene-1,6-dioxa-2-azaspiro [4.4] nona-2,8-diene skeleton along with, in some cases, the predictable oxime. The structures of such spiro compounds were determined by 2D NMR spectroscopy. The suggested formation of this skeleton involves an in situ oximation/dehydration/S_N' cascade reaction.

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从取代的酮糠醇中意外生成螺异噁唑啉-二氢呋喃化合物。

在盐酸羟胺和吡啶存在下，以乙醇为溶剂对取代的酮福尔醇进行氧化，产生了一类新的螺衍生物，其骨架为 7-亚甲基-1,6-二氧杂-2-氮杂螺[4.4]壬-2,8-二烯，在某些情况下还有可预测的肟。这些螺化合物的结构是通过二维核磁共振光谱测定的。这种骨架的形成涉及原位氧化/脱水/SN'级联反应。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Molecules 化学-有机化学

CiteScore

7.40

自引率

8.70%

发文量

7524

审稿时长

1.4 months

期刊介绍： Molecules (ISSN 1420-3049, CODEN: MOLEFW) is an open access journal of synthetic organic chemistry and natural product chemistry. All articles are peer-reviewed and published continously upon acceptance. Molecules is published by MDPI, Basel, Switzerland. Our aim is to encourage chemists to publish as much as possible their experimental detail, particularly synthetic procedures and characterization information. There is no restriction on the length of the experimental section. In addition, availability of compound samples is published and considered as important information. Authors are encouraged to register or deposit their chemical samples through the non-profit international organization Molecular Diversity Preservation International (MDPI). Molecules has been launched in 1996 to preserve and exploit molecular diversity of both, chemical information and chemical substances.