从取代茚†合成2,3-苯二氮卓类药物的简单途径

IF 2.7 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2025-04-08 DOI:10.1039/d5ob00361j

Ekaterina S. Tarasova , Olga V. Shurupova , Sergey A. Rzhevskiy , Lidiya I. Minaeva , Maxim A. Topchiy , Andrey F. Asachenko

{"title":"从取代茚†合成2,3-苯二氮卓类药物的简单途径","authors":"Ekaterina S. Tarasova , Olga V. Shurupova , Sergey A. Rzhevskiy , Lidiya I. Minaeva , Maxim A. Topchiy , Andrey F. Asachenko","doi":"10.1039/d5ob00361j","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, we present a two-step approach for synthesizing 2,3-benzodiazepines from substituted indenes. This process involves oxidation of indenes to 1,5-diketones followed by their cyclocondensation with hydrazine hydrate. The optimized conditions for a wide range of substituted 2,3-benzodiazepines, including the well-known anxiolytic tofisopam, were investigated. A detailed mechanism for the cyclization of 1,5-diketones with hydrazine hydrate was established using <sup>1</sup>H NMR kinetic experiments.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 19","pages":"Pages 4710-4717"},"PeriodicalIF":2.7000,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"A simple route to 2,3-benzodiazepines from substituted indenes†\",\"authors\":\"Ekaterina S. Tarasova , Olga V. Shurupova , Sergey A. Rzhevskiy , Lidiya I. Minaeva , Maxim A. Topchiy , Andrey F. Asachenko\",\"doi\":\"10.1039/d5ob00361j\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Herein, we present a two-step approach for synthesizing 2,3-benzodiazepines from substituted indenes. This process involves oxidation of indenes to 1,5-diketones followed by their cyclocondensation with hydrazine hydrate. The optimized conditions for a wide range of substituted 2,3-benzodiazepines, including the well-known anxiolytic tofisopam, were investigated. A detailed mechanism for the cyclization of 1,5-diketones with hydrazine hydrate was established using <sup>1</sup>H NMR kinetic experiments.</div></div>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\"23 19\",\"pages\":\"Pages 4710-4717\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2025-04-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1477052025003040\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025003040","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

在这里，我们提出了一种两步法从取代的茚合成2,3-苯二氮卓类药物。这个过程包括将茚酮氧化为1,5-二酮，然后与水合肼进行环缩合。研究了一系列取代的2,3-苯二氮卓类药物，包括著名的抗焦虑药托非索泮的优化条件。通过1H NMR动力学实验，建立了1,5-二酮与水合肼环化的详细机理。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

A simple route to 2,3-benzodiazepines from substituted indenes†

Herein, we present a two-step approach for synthesizing 2,3-benzodiazepines from substituted indenes. This process involves oxidation of indenes to 1,5-diketones followed by their cyclocondensation with hydrazine hydrate. The optimized conditions for a wide range of substituted 2,3-benzodiazepines, including the well-known anxiolytic tofisopam, were investigated. A detailed mechanism for the cyclization of 1,5-diketones with hydrazine hydrate was established using ¹H NMR kinetic experiments.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.