{"title":"Stereo- and regioselectivity in nitrile oxide cycloaddition reactions to norethisterone acetate as dipolarophile","authors":"Giuseppe Faita , Mariella Mella , Paolo Quadrelli","doi":"10.1016/j.steroids.2025.109598","DOIUrl":null,"url":null,"abstract":"<div><div>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.</div></div>","PeriodicalId":21997,"journal":{"name":"Steroids","volume":"217 ","pages":"Article 109598"},"PeriodicalIF":2.1000,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Steroids","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0039128X2500039X","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
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.
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.
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