Stereo- and regioselectivity in nitrile oxide cycloaddition reactions to norethisterone acetate as dipolarophile

IF 2.1 4区医学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Steroids Pub Date : 2025-03-15 DOI:10.1016/j.steroids.2025.109598

Giuseppe Faita , Mariella Mella , Paolo Quadrelli

引用次数: 0

Abstract

Benzo- and anthracenenitrile oxides undergo 1,3-dipolar cycloaddition reactions with 17 α- acetate norethisterone affording the expected isoxazoline and isoxazoles derivatives in good yields and as single regioisomers. The structures of all the new compounds were elucidated on the basis of the corresponding analytical and spectroscopic data, which were presented and discussed. The stereo- and regiochemical outcome of the cycloadditions were also accounted on the basis of 1,3-dipolar cycloaddition theory and computational investigations. Electronic (Frontier Orbital theory) and steric effects are at work in orienting selectively the cycloaddition to specific regioisomeric steroids.

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偶极亲和剂醋酸去甲甾酮在氧化腈环加成反应中的立体选择性和区域选择性

苯并和蒽杂腈氧化物与17 α-醋酸去甲甾酮发生1,3-偶极环加成反应，得到预期的异恶唑啉和异恶唑衍生物，收率高，且为单区域异构体。根据相应的分析和光谱数据，对所有新化合物的结构进行了阐述，并进行了讨论。在1,3偶极环加成理论和计算研究的基础上，讨论了环加成的立体化学和区域化学结果。电子（前沿轨道理论）和空间效应在选择性地定向环加成到特定的区域异构体类固醇中起作用。

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

Steroids 医学-内分泌学与代谢

CiteScore

5.10

自引率

3.70%

发文量

120

审稿时长

73 days

期刊介绍： STEROIDS is an international research journal devoted to studies on all chemical and biological aspects of steroidal moieties. The journal focuses on both experimental and theoretical studies on the biology, chemistry, biosynthesis, metabolism, molecular biology, physiology and pharmacology of steroids and other molecules that target or regulate steroid receptors. Manuscripts presenting clinical research related to steroids, steroid drug development, comparative endocrinology of steroid hormones, investigations on the mechanism of steroid action and steroid chemistry are all appropriate for submission for peer review. STEROIDS publishes both original research and timely reviews. For details concerning the preparation of manuscripts see Instructions to Authors, which is published in each issue of the journal.