• 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

2-氨基-1,3-苯并噻唑:α-碘代甲基酮的内烷基化反应及其随后的环化反应。

2-Amino-1,3-benzothiazole: Endo -Alkylation with α-Iodo Methyl Ketones Followed by Cyclization.

机构信息

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russia.

出版信息

Molecules. 2023 Feb 23;28(5):2093. doi: 10.3390/molecules28052093.

DOI:10.3390/molecules28052093
PMID:36903340
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10004639/
Abstract

Reactions of 2-amino-1,3-benzothiazole with aliphatic, aromatic and heteroaromatic α-iodoketones in the absence of bases or catalysts have been studied. The reaction proceeds by N-alkylation of the endocyclic nitrogen atom followed by intramolecular dehydrative cyclization. The regioselectivity is explained and the mechanism of the reaction is proposed. A number of new linear and cyclic iodide and triiodide benzothiazolium salts have been obtained and their structure proved by NMR and UV spectroscopy.

摘要

研究了 2-氨基-1,3-苯并噻唑与脂肪族、芳香族和杂环α-碘代酮在无碱或催化剂存在下的反应。该反应通过环内氮原子的 N-烷基化,然后进行分子内脱水环化进行。解释了区域选择性,并提出了反应机理。得到了一系列新的线性和环状碘化物和三碘化物苯并噻唑鎓盐,并通过 NMR 和 UV 光谱证明了它们的结构。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/10004639/7b35e5cd5043/molecules-28-02093-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/10004639/95778b6bff90/molecules-28-02093-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/10004639/69c65e91e7bd/molecules-28-02093-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/10004639/09c6f2301399/molecules-28-02093-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/10004639/7b35e5cd5043/molecules-28-02093-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/10004639/95778b6bff90/molecules-28-02093-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/10004639/69c65e91e7bd/molecules-28-02093-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/10004639/09c6f2301399/molecules-28-02093-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e1c1/10004639/7b35e5cd5043/molecules-28-02093-sch004.jpg

相似文献

1
2-Amino-1,3-benzothiazole: Endo -Alkylation with α-Iodo Methyl Ketones Followed by Cyclization.2-氨基-1,3-苯并噻唑:α-碘代甲基酮的内烷基化反应及其随后的环化反应。
Molecules. 2023 Feb 23;28(5):2093. doi: 10.3390/molecules28052093.
2
Asymmetric synthesis of unsaturated, fused bicyclic proline analogues through amino alkylation of cyclic bis(allylsulfoximine)titanium complexes and migratory cyclization of delta-amino alkenyl aminosulfoxonium salts.通过环状双(烯丙基亚砜亚胺)钛配合物的氨基烷基化和δ-氨基烯基氨基亚砜鎓盐的迁移环化反应实现不饱和稠合双环脯氨酸类似物的不对称合成。
J Am Chem Soc. 2003 Oct 29;125(43):13243-51. doi: 10.1021/ja030324y.
3
Sequenced reactions with samarium(II) iodide. Sequential intramolecular Barbier cyclization/Grob fragmentation for the synthesis of medium-sized carbocycles.与碘化钐(II)的序列反应。用于合成中等大小碳环的顺序分子内巴比耶环化/格罗布碎片化反应。
J Org Chem. 2001 Jun 29;66(13):4511-6. doi: 10.1021/jo001513r.
4
Sequenced reactions with samarium(II) iodide. Sequential intramolecular Reformatsky/nucleophilic acyl substitution reactions for the synthesis of medium-sized carbocycles.与碘化钐(II)的序列反应。用于合成中等大小碳环的顺序分子内Reformatsky/亲核酰基取代反应。
J Org Chem. 2002 May 17;67(10):3459-63. doi: 10.1021/jo020027w.
5
Catalyst-free dehydrative α-alkylation of ketones with alcohols: green and selective autocatalyzed synthesis of alcohols and ketones.无催化剂促进的酮与醇的脱水 α-烷基化反应:醇和酮的绿色、选择性自催化合成。
Angew Chem Int Ed Engl. 2014 Jan 3;53(1):225-9. doi: 10.1002/anie.201308642. Epub 2013 Nov 24.
6
Cyclometalated Ruthenium Pincer Complexes as Catalysts for the α-Alkylation of Ketones with Alcohols.环金属化钌钳形配合物作为酮与醇进行α-烷基化反应的催化剂
Chemistry. 2020 May 12;26(27):6050-6055. doi: 10.1002/chem.202000396. Epub 2020 Mar 9.
7
Asymmetric synthesis of a CBI-based cyclic N-acyl O-amino phenol duocarmycin prodrug.一种基于CBI的环状N-酰基O-氨基苯酚多卡霉素前药的不对称合成。
J Org Chem. 2014 Oct 17;79(20):9699-703. doi: 10.1021/jo501839x. Epub 2014 Oct 3.
8
A new strategy for the synthesis of 1,4-benzodiazepine derivatives based on the tandem N-alkylation-ring opening-cyclization reactions of methyl 1-arylaziridine-2-carboxylates with N-[2-bromomethyl(phenyl)]trifluoroacetamides.一种基于1-芳基氮杂环丙烷-2-羧酸甲酯与N-[2-(溴甲基)(苯基)]三氟乙酰胺的串联N-烷基化-开环-环化反应合成1,4-苯并二氮杂卓衍生物的新策略。
J Org Chem. 2008 Mar 7;73(5):1979-82. doi: 10.1021/jo7024306. Epub 2008 Jan 30.
9
Superacid-catalyzed intramolecular cyclization reaction of arylcyanopropionate: geminal substitution effect on superelectrophilicity.芳基氰基丙酸酯的超强酸催化分子内环化反应:偕二取代对超亲电性的影响
J Org Chem. 2008 Jun 6;73(11):4219-24. doi: 10.1021/jo800674h. Epub 2008 May 14.
10
Quantitating the effect of an ortho substituent on cyclization and intramolecular hydrogen-transfer reactions of aryl radicals.定量邻位取代基对芳基自由基环化及分子内氢转移反应的影响。
J Org Chem. 2003 Apr 4;68(7):2972-4. doi: 10.1021/jo0268759.

本文引用的文献

1
On water catalyst-free synthesis of benzo[]imidazo[2,1-] thiazoles and novel -alkylated 2-aminobenzo[]oxazoles under microwave irradiation.微波辐射下无催化剂水相合成苯并[]咪唑并[2,1-]噻唑及新型 -烷基化2-氨基苯并[]恶唑
RSC Adv. 2020 Jan 3;10(2):770-778. doi: 10.1039/c9ra08929b. eCollection 2020 Jan 2.
2
3-Methyl-imidazo[2,1-b]thiazole derivatives as a new class of antifolates: Synthesis, in vitro/in vivo bio-evaluation and molecular modeling simulations.3-甲基-咪唑并[2,1-b]噻唑衍生物作为一类新型抗叶酸剂:合成、体内外生物评价及分子模拟研究。
Bioorg Chem. 2021 Oct;115:105205. doi: 10.1016/j.bioorg.2021.105205. Epub 2021 Jul 24.
3
Nanomolar potency of imidazo[2,1-b]thiazole analogs as indoleamine 2,3-dioxygenase inhibitors.
作为吲哚胺 2,3-双加氧酶抑制剂的咪唑并[2,1-b]噻唑类似物的纳摩尔效力。
Arch Pharm (Weinheim). 2021 Nov;354(11):e2100202. doi: 10.1002/ardp.202100202. Epub 2021 Jul 27.
4
Modern Approaches to the Synthesis and Transformations of Practically Valuable Benzothiazole Derivatives.现代方法合成与转化实用价值的苯并噻唑衍生物。
Molecules. 2021 Apr 10;26(8):2190. doi: 10.3390/molecules26082190.
5
Antioxidant activity of novel imidazo[2,1-b]thiazole derivatives: Design, synthesis, biological evaluation, molecular docking study and in silico ADME prediction.新型咪唑并[2,1-b]噻唑衍生物的抗氧化活性:设计、合成、生物评价、分子对接研究和计算机 ADME 预测。
Bioorg Chem. 2020 Oct;103:104220. doi: 10.1016/j.bioorg.2020.104220. Epub 2020 Aug 26.
6
Synthesis and Biological Evaluation of Imidazo[2 ,1-]Thiazole based Sulfonyl Piperazines as Novel Carbonic Anhydrase II Inhibitors.基于咪唑并[2,1 - ]噻唑的磺酰基哌嗪类新型碳酸酐酶II抑制剂的合成与生物学评价
Metabolites. 2020 Mar 31;10(4):136. doi: 10.3390/metabo10040136.
7
Design and synthesis of novel Imidazo[2,1-b]thiazole derivatives as potent antiviral and antimycobacterial agents.设计和合成新型咪唑并[2,1-b]噻唑衍生物作为有效的抗病毒和抗分枝杆菌药物。
Bioorg Chem. 2020 Jan;95:103496. doi: 10.1016/j.bioorg.2019.103496. Epub 2019 Dec 6.
8
Synthesis of new 1,3-thiazol derivatives of maleopimaric acid as anticancer, antibacterial and antifungal agents.合成新型马来海松酸 1,3-噻唑衍生物作为抗癌、抗菌和抗真菌剂。
Nat Prod Res. 2021 Apr;35(8):1340-1348. doi: 10.1080/14786419.2019.1648459. Epub 2019 Aug 20.
9
Synthesis of novel derivatives of 7,8-dihydro-6H-imidazo[2,1-b][1,3]benzothiazol-5-one and their virus-inhibiting activity against influenza A virus.新型 7,8-二氢-6H-咪唑并[2,1-b][1,3]苯并噻唑-5-酮衍生物的合成及其抗流感 A 病毒活性。
Arch Pharm (Weinheim). 2019 Feb;352(2):e1800225. doi: 10.1002/ardp.201800225. Epub 2018 Dec 6.
10
Synthesis of Benzo[d]imidazo[2,1-b]thiazole-Propenone Conjugates as Cytotoxic and Apoptotic Inducing Agents.苯并[d]咪唑并[2,1-b]噻唑-丙烯酮轭合物的合成及其作为细胞毒性和诱导细胞凋亡的试剂。
Anticancer Agents Med Chem. 2019;19(3):347-355. doi: 10.2174/1871520619666181127112621.