• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

由2-溴-(2/3-取代苯基)-1-茚-1,3(2)-二酮衍生的新型11-苯并[5,6][1,4]噻嗪并[3,4 -]异吲哚-11-酮的便捷高效合成

Convenient and efficient synthesis of novel 11-benzo[5,6][1,4]thiazino[3,4-]isoindol-11-ones derived from 2-bromo-(2/3-substitutedphenyl)-1-indene-1,3(2)-diones.

作者信息

Mor Satbir, Sindhu Suchita

机构信息

Department of Chemistry, Guru Jambheshwar University of Science & Technology Hisar-125001 Haryana India

出版信息

RSC Adv. 2019 Apr 25;9(23):12784-12792. doi: 10.1039/c9ra02403d.

DOI:10.1039/c9ra02403d
PMID:35557558
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9092632/
Abstract

An unprecedented formation of 11-benzo[5,6][1,4]thiazino[3,4-]isoindol-11-ones through a one-step reaction of differently substituted 2-aminobenzenethiols and 2-bromo-(2/3-substitutedphenyl)-1-indene-1,3(2)-diones in freshly dried ethanol under reflux conditions has been investigated. This unique transformation probably occurs through an initial nucleophilic substitution followed by ring opening and subsequent intramolecular cyclization. The structures of all the synthesized benzo[1,4]thiazino isoindolinones were established by FTIR, H NMR, C NMR, HRMS, and X-ray crystallographic analysis. This approach was found to be simple and convenient and provides several advantages such as substantial atom economy, short reaction time and operational simplicity.

摘要

通过不同取代的2-氨基苯硫醇与2-溴-（2/3-取代苯基）-1-茚-1,3（2）-二酮在新鲜干燥的乙醇中回流条件下的一步反应，实现了前所未有的11-苯并[5,6][1,4]噻嗪并[3,4-]异吲哚-11-酮的合成。研究了这种独特的转化过程，可能是通过初始的亲核取代，随后开环并进行分子内环化。所有合成的苯并[1,4]噻嗪并异吲哚啉酮的结构均通过傅里叶变换红外光谱（FTIR）、氢核磁共振（H NMR）、碳核磁共振（C NMR）、高分辨率质谱（HRMS）和X射线晶体学分析得以确定。该方法被发现简单方便，具有原子经济性高、反应时间短和操作简便等优点。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ca7/9092632/74856691412a/c9ra02403d-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ca7/9092632/8e15f7eddbb3/c9ra02403d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ca7/9092632/c492214f72f0/c9ra02403d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ca7/9092632/5b8e3f025d56/c9ra02403d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ca7/9092632/cec29a21d819/c9ra02403d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ca7/9092632/74856691412a/c9ra02403d-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ca7/9092632/8e15f7eddbb3/c9ra02403d-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ca7/9092632/c492214f72f0/c9ra02403d-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ca7/9092632/5b8e3f025d56/c9ra02403d-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ca7/9092632/cec29a21d819/c9ra02403d-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ca7/9092632/74856691412a/c9ra02403d-s4.jpg

相似文献

1
Convenient and efficient synthesis of novel 11-benzo[5,6][1,4]thiazino[3,4-]isoindol-11-ones derived from 2-bromo-(2/3-substitutedphenyl)-1-indene-1,3(2)-diones.由2-溴-(2/3-取代苯基)-1-茚-1,3(2)-二酮衍生的新型11-苯并[5,6][1,4]噻嗪并[3,4 -]异吲哚-11-酮的便捷高效合成
RSC Adv. 2019 Apr 25;9(23):12784-12792. doi: 10.1039/c9ra02403d.
2
Convenient synthesis of benzothiazinoisoindol-11-ones and benzoindenothiazin-11-ones, and antimicrobial testing thereof.苯并噻嗪异吲哚-11-酮和苯并茚并噻嗪-11-酮的简便合成及其抗菌测试。
Mol Divers. 2023 Jun;27(3):1223-1241. doi: 10.1007/s11030-022-10483-9. Epub 2022 Aug 3.
3
Reactions of 3-Hydroxy-2-phenyl-1-benzo[]isoindol-1-one: A Route to 3-Hydroxy-/3-anilinobenzo[]indan-1-ones and Benzo[]phthalazin-1(2)-ones.3-羟基-2-苯基-1-苯并[I]异吲哚-1-酮的反应：合成 3-羟基-/3-苯胺基苯并[I]茚-1-酮和苯并[I]酞嗪-1(2)-酮的途径。
Molecules. 2022 Nov 29;27(23):8319. doi: 10.3390/molecules27238319.
4
Thietanyl Protection in the Synthesis of 8-Substituted 1-Benzyl-3-methyl-3,7-dihydro- 1H-purine-2,6-diones.四氮杂环十五烷保护在 8-取代 1-苄基-3-甲基-3,7-二氢-1H-嘌呤-2,6-二酮合成中的应用。
Curr Org Synth. 2020;17(7):535-539. doi: 10.2174/1570179417666200628015511.
5
Cascade Reaction of 1,1-Enediamines with 2-Benzylidene-1-indene-1,3(2)-diones: Selective Synthesis of Indenodihydropyridine and Indenopyridine Compounds.1,1-烯二胺与2-亚苄基-1-茚-1,3(2)-二酮的串联反应：茚并二氢吡啶和茚并吡啶化合物的选择性合成
ACS Omega. 2019 Apr 11;4(4):6637-6646. doi: 10.1021/acsomega.9b00407. eCollection 2019 Apr 30.
6
Unsymmetrically Substituted Dibenzo[][1,5]-diazocine-6,12(5,11)dione-A Convenient Scaffold for Bioactive Molecule Design.不对称取代二苯并[][1,5]二氮杂环辛烷-6,12(5,11)-二酮——生物活性分子设计的一种便捷骨架。
Molecules. 2020 Feb 18;25(4):906. doi: 10.3390/molecules25040906.
7
Synthesis, in vitro protoporphyrinogen oxidase inhibition, and herbicidal activity of N-(benzothiazol-5-yl)hexahydro-1H-isoindole-1,3-diones and N-(benzothiazol-5-yl)hexahydro-1H-isoindol-1-ones.N-(苯并噻唑-5-基)六氢-1H-异吲哚-1,3-二酮和N-(苯并噻唑-5-基)六氢-1H-异吲哚-1-酮的合成、体外原卟啉原氧化酶抑制作用及除草活性
Chem Biol Drug Des. 2014 Oct;84(4):431-42. doi: 10.1111/cbdd.12331. Epub 2014 May 12.
8
Biradicals from benzoenyne-allenes. Application in the synthesis of 11H-benzo[b]fluoren-11-ols, 1H-cyclobut[a]indenes, and related compounds.苯并烯炔-丙二烯产生的双自由基。在11H-苯并[b]芴-11-醇、1H-环丁[a]茚及相关化合物合成中的应用。
J Org Chem. 2001 Oct 5;66(20):6662-8. doi: 10.1021/jo0104577.
9
Copper-Catalyzed Cascade 1,4-Addition/Annulation/Hydrolysis of Propargylamines with 2-Hydroxynaphthalene-1,4-diones: Direct Formation of 12-Phenacyl-11-benzo[]xanthenes.铜催化的炔丙胺与 2-羟基萘-1,4-二酮的 1,4-加成/环化/水解反应：直接形成 12-苯并[]氧杂蒽-11-基-11-苯甲酰基。
J Org Chem. 2021 Mar 5;86(5):4182-4192. doi: 10.1021/acs.joc.0c03029. Epub 2021 Feb 24.
10
Syntheses of 3-[(Alkylamino)methylene]-6-methylpyridine-2,4(1,3)-diones, 3-Substituted 7-Methyl-2-pyrano[3,2-]pyridine-2,5(6)-dione Fluorescence Probes, and Tetrahydro-1,9-2,10-dioxa-9-azaanthracen-1-ones.3-[(烷基氨基)亚甲基]-6-甲基吡啶-2,4(1,3)-二酮、3-取代的7-甲基-2-吡喃并[3,2-]吡啶-2,5(6)-二酮荧光探针及四氢-1,9-2,10-二氧杂-9-氮杂蒽-1-酮的合成
Synthesis (Stuttg). 2014 Aug;46(16):2179-2190. doi: 10.1055/s-0033-1339027.

本文引用的文献

1
AIBN-Promoted Synthesis of Bibenzo[ b][1,4]thiazines by the Condensation of 2,2'-Dithiodianiline with Methyl Aryl Ketones.AIBN 促进的 2,2'-二硫二苯胺与甲基芳基酮缩合合成双苯并[b][1,4]噻嗪
Org Lett. 2018 Jun 1;20(11):3332-3336. doi: 10.1021/acs.orglett.8b01238. Epub 2018 May 17.
2
10-3,6-Diazaphenothiazine induces G/M phase cell cycle arrest and caspase-dependent apoptosis and inhibits cell invasion of A2780 ovarian carcinoma cells through the regulation of NF-κB and (BIRC6-XIAP) complexes.10-3,6-二氮杂吩噻嗪通过调节核因子κB和（杆状病毒IAP重复序列6-X连锁凋亡抑制蛋白）复合物，诱导A2780卵巢癌细胞的G/M期细胞周期阻滞和半胱天冬酶依赖性凋亡，并抑制其细胞侵袭。
Drug Des Devel Ther. 2017 Oct 24;11:3045-3063. doi: 10.2147/DDDT.S144415. eCollection 2017.
3
Method for the Synthesis of Phenothiazines via a Domino Iron-Catalyzed C-S/C-N Cross-Coupling Reaction.通过多米诺铁催化的C-S/C-N交叉偶联反应合成吩噻嗪的方法。
J Org Chem. 2015 Jun 19;80(12):6128-32. doi: 10.1021/acs.joc.5b00568. Epub 2015 Jun 9.
4
Synthesis, spectral characterization, and pharmacological importance of new 4H-1,4-benzothiazines, their sulfone analogues, and ribofuranosides.新型4H-1,4-苯并噻嗪及其砜类似物和呋喃核糖苷的合成、光谱表征及药理学重要性
Nucleosides Nucleotides Nucleic Acids. 2015;34(1):40-55. doi: 10.1080/15257770.2014.955194.
5
6-Substituted 9-fluoroquino[3,2-b]benzo[1,4]thiazines display strong antiproliferative and antitumor properties.6-取代 9-氟喹诺[3,2-b]苯并[1,4]噻嗪具有很强的抗增殖和抗肿瘤特性。
Eur J Med Chem. 2015 Jan 7;89:411-20. doi: 10.1016/j.ejmech.2014.10.070. Epub 2014 Oct 24.
6
Synthesis and antitubercular screening of some novel 4H-1,4- benzothiazines and their sulfones under environment benign solvent free conditions as future anti-tubercular agents.在环境友好的无溶剂条件下合成一些新型4H-1,4-苯并噻嗪及其砜类化合物并进行抗结核筛选，作为未来的抗结核药物。
Comb Chem High Throughput Screen. 2015;18(1):48-52. doi: 10.2174/1386207317666141126164147.
7
Copper(I)-catalyzed oxidative coupling between 2-aminobenzothiazole and terminal alkyne: formation of benzothiazine.铜（I）催化 2-氨基苯并噻唑与末端炔烃的氧化偶联反应：苯并噻嗪的形成。
Org Lett. 2014 Nov 7;16(21):5652-5. doi: 10.1021/ol502729c. Epub 2014 Oct 17.
8
Discovery of a tetracyclic quinoxaline derivative as a potent and orally active multifunctional drug candidate for the treatment of neuropsychiatric and neurological disorders.发现一种四环喹喔啉衍生物，作为一种强效的、可口服的多功能药物候选物，用于治疗神经精神和神经退行性疾病。
J Med Chem. 2014 Mar 27;57(6):2670-82. doi: 10.1021/jm401958n. Epub 2014 Mar 5.
9
Highly Regioselective Synthesis of Substituted Isoindolinones Ruthenium-Catalyzed Alkyne Cyclotrimerizations.取代异吲哚啉酮的高度区域选择性合成：钌催化的炔烃环三聚反应
Adv Synth Catal. 2013 Aug 12;355(11-12):2353-2360. doi: 10.1002/adsc.201300055.
10
Efficient synthesis of a (Z)-3-methyleneisoindolin-1-one library using Cu(OAc)₂•H₂O/DBU under microwave irradiation.在微波辐射下使用 Cu(OAc)₂•H₂O/DBU 高效合成 (Z)-3-亚甲基异吲哚啉-1-酮库。
Molecules. 2013 Jan 4;18(1):654-65. doi: 10.3390/molecules18010654.