由磺酰基肼和活化酰胺合成 N-酰基-N'-磺酰基肼

Synthesis Pub Date : 2024-07-16 DOI:10.1055/a-2367-2505
Yubin An, Jonghoon Oh, Sunwoo Lee
{"title":"由磺酰基肼和活化酰胺合成 N-酰基-N'-磺酰基肼","authors":"Yubin An, Jonghoon Oh, Sunwoo Lee","doi":"10.1055/a-2367-2505","DOIUrl":null,"url":null,"abstract":"A methodology was developed for synthesizing acyl sulfonyl hydrazides through acyl substitution reactions between activated amides and arylsulfonyl hydrazides. Optimization of the reaction conditions revealed that using Cs₂CO₃ as a base and 1,4-dioxane as a solvent at 25 °C for 12 h produced the highest yields. Among various amides tested, N-benzoylsuccinimide was found to be the most reactive, with reduced reactivity observed for N-mesityl, N-tosyl and N-Boc substituted tertiary benzoyl amides. Cross-reactions between a diverse range of N-benzoylsuccinimides and arylsulfonyl hydrazides successfully produced the corresponding N-acyl-N’-sulfonyl hydrazides with yields ranging from 63% to 93%.","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis of N-Acyl-N’-Sulfonyl Hydrazides from Sulfonyl Hydrazides and Activated Amides\",\"authors\":\"Yubin An, Jonghoon Oh, Sunwoo Lee\",\"doi\":\"10.1055/a-2367-2505\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A methodology was developed for synthesizing acyl sulfonyl hydrazides through acyl substitution reactions between activated amides and arylsulfonyl hydrazides. Optimization of the reaction conditions revealed that using Cs₂CO₃ as a base and 1,4-dioxane as a solvent at 25 °C for 12 h produced the highest yields. Among various amides tested, N-benzoylsuccinimide was found to be the most reactive, with reduced reactivity observed for N-mesityl, N-tosyl and N-Boc substituted tertiary benzoyl amides. Cross-reactions between a diverse range of N-benzoylsuccinimides and arylsulfonyl hydrazides successfully produced the corresponding N-acyl-N’-sulfonyl hydrazides with yields ranging from 63% to 93%.\",\"PeriodicalId\":501298,\"journal\":{\"name\":\"Synthesis\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-07-16\",\"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-2367-2505\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2367-2505","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

摘要

通过活化酰胺和芳基磺酰肼之间的酰基取代反应,开发了一种合成酰基磺酰肼的方法。优化反应条件后发现,以 Cs₂CO₃为碱,1,4-二氧六环为溶剂,在 25 °C 下反应 12 小时的产率最高。在测试的各种酰胺中,发现 N-苯甲酰基琥珀酰亚胺的反应性最强,而 N-甲磺酰基、N-对甲磺酰基和 N-Boc 取代的叔苯甲酰基酰胺的反应性则较弱。各种 N-苯甲酰基琥珀酰亚胺与芳基磺酰肼之间的交叉反应成功地生成了相应的 N-酰基-N'-磺酰肼,产率为 63% 至 93%。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
Synthesis of N-Acyl-N’-Sulfonyl Hydrazides from Sulfonyl Hydrazides and Activated Amides
A methodology was developed for synthesizing acyl sulfonyl hydrazides through acyl substitution reactions between activated amides and arylsulfonyl hydrazides. Optimization of the reaction conditions revealed that using Cs₂CO₃ as a base and 1,4-dioxane as a solvent at 25 °C for 12 h produced the highest yields. Among various amides tested, N-benzoylsuccinimide was found to be the most reactive, with reduced reactivity observed for N-mesityl, N-tosyl and N-Boc substituted tertiary benzoyl amides. Cross-reactions between a diverse range of N-benzoylsuccinimides and arylsulfonyl hydrazides successfully produced the corresponding N-acyl-N’-sulfonyl hydrazides with yields ranging from 63% to 93%.
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
自引率
0.00%
发文量
0
期刊最新文献
Facile Synthesis of Silanols via Cesium Carbonate Catalyzed Hydrosilanes with Water Discovery Process Chemistry: An Innovation Hub at the Interface of Academia, the Pharmaceutical Industry, and Contract Research Organization Accessing a Medicinal-Chemistry-Relevant Chemical Space with sp2–sp3 Hybrid Heterocyclic Fragments Recent Advances in Diazophosphonate Chemistry: Reactions and Transformations Recent Advances in Fluoroalkylation Strategies: Exploring Novel Reactivities and Synthetic Applications of Sulfone- and Sulfinate-Based Reagents for Mono-, Di-, and Trifluoromethylations
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1