Alexandr Mandzhulo, Iryna Vashchenko, Oleg Lukin, Svetlana Shishkina, Grygoriy Dolgonos, Andrii Gerasov, Vitaliy Yepishev, Dariia Samofalova, Volodymyr Fetyukhin, Alexander Shivanyuk
{"title":"Spirocyclic Hybrids of Nortropane and 1,3-Oxazinan-2-one Fragments","authors":"Alexandr Mandzhulo, Iryna Vashchenko, Oleg Lukin, Svetlana Shishkina, Grygoriy Dolgonos, Andrii Gerasov, Vitaliy Yepishev, Dariia Samofalova, Volodymyr Fetyukhin, Alexander Shivanyuk","doi":"10.1055/a-2335-4444","DOIUrl":null,"url":null,"abstract":"<p>We report facile and versatile procedures for the synthesis of <i>exo</i>- and <i>endo</i>-isomeric spirocyclic hybrids of pharmacophoric (1<i>R</i>,5<i>S</i>)-8-azabicyclo[3.2.1]octane (nortropane) and 1,3-oxazinan-2-one fragments. Our approach consists of the hydrocyanation of <i>endo</i>- and <i>exo</i>-isomeric <i>N</i>-Cbz-protected nortropane-3-spiroepoxides, the reduction of hydroxy nitriles into amino alcohols, the synthesis of <i>N</i>-alkylated amino alcohols <i>via</i> reductive amination, the spirocyclization of the amino alcohols, <i>N</i>-alkylation of the unsubstituted 1,3-oxazinan-2-one fragment in the spiro compounds, and removal of the Cbz protecting groups.</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"17 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2335-4444","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
We report facile and versatile procedures for the synthesis of exo- and endo-isomeric spirocyclic hybrids of pharmacophoric (1R,5S)-8-azabicyclo[3.2.1]octane (nortropane) and 1,3-oxazinan-2-one fragments. Our approach consists of the hydrocyanation of endo- and exo-isomeric N-Cbz-protected nortropane-3-spiroepoxides, the reduction of hydroxy nitriles into amino alcohols, the synthesis of N-alkylated amino alcohols via reductive amination, the spirocyclization of the amino alcohols, N-alkylation of the unsubstituted 1,3-oxazinan-2-one fragment in the spiro compounds, and removal of the Cbz protecting groups.
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