• 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

铑（III）催化3-苯基-1,2,4-恶二唑与2-重氮-1,3-二酮的双环化反应：合成吡喃并异喹啉类化合物

Rh(III)-Catalyzed Double Annulation of 3-Phenyl-1,2,4-oxadiazoles with 2-Diazo-1,3-diketones: Access to Pyran-Fused Isoquinolines.

作者信息

Zhang Enshen, Sun Mei, Gao Lvlv

机构信息

School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China.

出版信息

Molecules. 2025 Jan 2;30(1):149. doi: 10.3390/molecules30010149.

DOI:10.3390/molecules30010149
PMID:39795205
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11721317/
Abstract

Efficient access to pyranoisoquinoline derivatives via rhodium-catalyzed double C-H functionalization of phenyl oxadiazoles and diazo compounds has been developed. Two C-C bonds and one C-O and C-N bond formation was realized by this tandem reaction, along with the formation of two heterocycles, affording diversified pyran-fused isoquinolines in moderate to good yields with broad functional group tolerance under mild reaction conditions.

摘要

通过铑催化的苯基恶二唑和重氮化合物的双C-H官能团化反应，实现了对吡喃异喹啉衍生物的高效合成。该串联反应实现了两个C-C键、一个C-O键和一个C-N键的形成，同时形成了两个杂环，在温和的反应条件下，以中等至良好的产率提供了具有广泛官能团耐受性的多种吡喃并异喹啉类化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/3e4f3a2d0fc6/molecules-30-00149-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/b8fa59e81866/molecules-30-00149-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/2c96570989a3/molecules-30-00149-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/5fd5a90a667e/molecules-30-00149-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/a4ca2cfc73cd/molecules-30-00149-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/3b9c2cbb9b28/molecules-30-00149-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/aff966a993b2/molecules-30-00149-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/3e4f3a2d0fc6/molecules-30-00149-sch006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/b8fa59e81866/molecules-30-00149-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/2c96570989a3/molecules-30-00149-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/5fd5a90a667e/molecules-30-00149-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/a4ca2cfc73cd/molecules-30-00149-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/3b9c2cbb9b28/molecules-30-00149-sch004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/aff966a993b2/molecules-30-00149-sch005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/39db/11721317/3e4f3a2d0fc6/molecules-30-00149-sch006.jpg

相似文献

1
Rh(III)-Catalyzed Double Annulation of 3-Phenyl-1,2,4-oxadiazoles with 2-Diazo-1,3-diketones: Access to Pyran-Fused Isoquinolines.铑（III）催化3-苯基-1,2,4-恶二唑与2-重氮-1,3-二酮的双环化反应：合成吡喃并异喹啉类化合物
Molecules. 2025 Jan 2;30(1):149. doi: 10.3390/molecules30010149.
2
Rh(III)-Catalyzed Cascade Annulation/C-H Activation of o-Ethynylanilines with Diazo Compounds: One-Pot Synthesis of Benzo[a]carbazoles via 1,4-Rhodium Migration.铑（III）催化的邻乙炔基苯胺与重氮化合物的串联环化/C-H活化：通过1,4-铑迁移一锅法合成苯并[a]咔唑
Org Lett. 2016 Oct 21;18(20):5236-5239. doi: 10.1021/acs.orglett.6b02534. Epub 2016 Oct 5.
3
Additive-Driven Rhodium-Catalyzed [4+1]/[4+2] Annulations of N-Arylphthalazine-1,4-dione with α-Diazo Carbonyl Compounds.添加剂驱动的铑催化 N-芳基酞嗪-1,4-二酮与 α-重氮羰基化合物的[4+1]/[4+2]环化反应
J Org Chem. 2018 Oct 5;83(19):11661-11673. doi: 10.1021/acs.joc.8b01630. Epub 2018 Sep 18.
4
Selective Synthesis of Aminoisoquinolines via Rh(III)-Catalyzed C-H/N-H Bond Functionalization of N-Aryl Amidines with Cyclic 2-Diazo-1,3-diketones.通过铑（III）催化的N-芳基脒与环状2-重氮-1,3-二酮的C-H/N-H键官能团化选择性合成氨基异喹啉。
J Org Chem. 2018 Nov 2;83(21):13463-13472. doi: 10.1021/acs.joc.8b02286. Epub 2018 Oct 17.
5
Rh(III)-Catalyzed C-H Activation/Intramolecular Cyclization: Access to -Acyl-2,3-dihydro-1-carbazol-4(9)-ones from Cyclic 2-Diazo-1,3-diketones and -Arylamides.铑（III）催化的C-H活化/分子内环化反应：从环状2-重氮-1,3-二酮和芳酰胺合成β-酰基-2,3-二氢-1-咔唑-4（9）-酮
ACS Omega. 2017 Nov 30;2(11):8507-8516. doi: 10.1021/acsomega.7b01637.
6
Mechanism of Rhodium-Catalyzed C-H Functionalization: Advances in Theoretical Investigation.铑催化 C-H 功能化反应的机理：理论研究进展。
Acc Chem Res. 2017 Nov 21;50(11):2799-2808. doi: 10.1021/acs.accounts.7b00400. Epub 2017 Nov 7.
7
Rh(III)-Catalyzed Cascade Nucleophilic Addition/Annulation of 2-Diazo-1,3-diketones with 1,3-Dicarbonyl Compounds To Access 6,7-Dihydrobenzofuran-4(5)-ones.铑（III）催化的2-重氮-1,3-二酮与1,3-二羰基化合物的级联亲核加成/环化反应以合成6,7-二氢苯并呋喃-4（5）-酮
J Org Chem. 2021 Jun 4;86(11):7370-7380. doi: 10.1021/acs.joc.1c00259. Epub 2021 May 20.
8
Rh(III)-catalysed C-H annulation of -stilbene acids with 2-diazo-1,3-diketones: facile access to 6,7-dihydrobenzofuran-4(5)-one and α-pyrone scaffolds.铑（III）催化的芪酸与2-重氮-1,3-二酮的C-H环化反应：便捷合成6,7-二氢苯并呋喃-4（5）-酮和α-吡喃酮骨架
Org Biomol Chem. 2024 May 15;22(19):3933-3939. doi: 10.1039/d4ob00151f.
9
Rh(III)-Catalyzed Defluorinative [4 + 2] Annulation of -Sulfonylarylamides with Ethyl 2-Diazo-3,3,3-trifluoropropanoate: Synthesis of 1,3,4-Functionalized Isoquinolines.Rh(III)-催化的 -磺酰芳基酰胺与乙基 2-重氮-3,3,3-三氟丙酸盐的脱氟 [4 + 2] 环加成反应：1,3,4-官能化异喹啉的合成。
Org Lett. 2022 Dec 16;24(49):8969-8974. doi: 10.1021/acs.orglett.2c03501. Epub 2022 Dec 1.
10
Rh(III)-catalyzed C(sp)-H functionalization/[4+2] annulation of oxadiazolones with iodonium ylides to access diverse fused-isoquinolines and fused-pyridines.铑（III）催化恶二唑酮与碘叶立德的C（sp）-H官能团化/[4+2]环化反应，以合成多种稠合异喹啉和稠合吡啶。
Chem Commun (Camb). 2024 Jun 20;60(51):6560-6563. doi: 10.1039/d4cc02046d.

引用本文的文献

1
Advanced QSPR modeling of profens using machine learning and molecular descriptors for NSAID analysis.使用机器学习和分子描述符对布洛芬类药物进行高级定量构效关系建模以用于非甾体抗炎药分析。
Sci Rep. 2025 Jul 20;15(1):26356. doi: 10.1038/s41598-025-09878-z.

本文引用的文献

1
Direct Assembly of Vinyl Fluorinated Isoquinolines Via Rh(III)-Catalyzed [4 + 2] Annulation.通过铑（III）催化的[4 + 2]环化反应直接组装乙烯基氟化异喹啉。
J Org Chem. 2023 Aug 4;88(15):10789-10800. doi: 10.1021/acs.joc.3c00826. Epub 2023 Jul 16.
2
Rh(III)-Catalyzed cascade annulation to produce an -acetyl chain of spiropyrroloisoquinoline derivatives.Rh(III)-催化级联环化反应生成 -乙酰链的螺吡咯并异喹啉衍生物。
Org Biomol Chem. 2022 Mar 16;20(11):2293-2299. doi: 10.1039/d2ob00137c.
3
Harnessing hypervalent iodonium ylides as carbene precursors: C-H activation of N-methoxybenzamides with a Rh(iii)-catalyst.
利用高价碘叶立德作为卡宾前体：用铑（III）催化剂实现N-甲氧基苯甲酰胺的C-H活化
Chem Commun (Camb). 2020 Dec 21;56(98):15462-15465. doi: 10.1039/d0cc06038k. Epub 2020 Nov 26.
4
Double -C-H Activation/Annulation of Benzamides with Aryl Alkynes: A Route to Double-Helical Polycyclic Heteroaromatics.
J Org Chem. 2019 Dec 6;84(23):15697-15705. doi: 10.1021/acs.joc.9b02339. Epub 2019 Nov 8.
5
One-Pot Unsymmetrical {[4 + 2] and [4 + 2]} Double Annulations of o/ o'-C-H Bonds of Arenes: Access to Unusual Pyranoisoquinolines.一锅法不对称 [4 + 2] 和 [4 + 2] 双环化 o/o'-C-H 键：获得不寻常的吡喃并异喹啉。
Org Lett. 2018 Sep 7;20(17):5144-5148. doi: 10.1021/acs.orglett.8b02068. Epub 2018 Aug 10.
6
Rhodium-Catalyzed Relay Carbenoid Functionalization of Aromatic C-H Bonds toward Fused Heteroarenes.铑催化的芳基 C-H 键重排卡宾官能团化反应构建稠合杂芳烃
Org Lett. 2018 Mar 2;20(5):1396-1399. doi: 10.1021/acs.orglett.8b00119. Epub 2018 Feb 22.
7
Rhodium(III)-Catalyzed Oxadiazole-Directed Alkenyl C-H Activation for Synthetic Access to 2-Acylamino and 2-Amino Pyridines.铑(III)催化恶二唑导向的烯基 C-H 活化用于合成 2-酰氨基和 2-氨基吡啶。
J Org Chem. 2017 Oct 6;82(19):9978-9987. doi: 10.1021/acs.joc.7b01303. Epub 2017 Sep 11.
8
Cobalt(III)-Catalyzed Oxadiazole-Directed C-H Activation for the Synthesis of 1-Aminoisoquinolines.钴(III)催化的噁二唑导向 C-H 活化合成 1-氨基异喹啉。
Org Lett. 2017 Jun 2;19(11):2885-2888. doi: 10.1021/acs.orglett.7b01119. Epub 2017 May 18.
9
Toxicological and pharmacological evaluation, antioxidant, ADMET and molecular modeling of selected racemic chromenotacrines {11-amino-12-aryl-8,9,10,12-tetrahydro-7H-chromeno[2,3-b]quinolin-3-ols} for the potential prevention and treatment of Alzheimer's disease.用于阿尔茨海默病潜在预防和治疗的选定外消旋色烯诺他克林{11-氨基-12-芳基-8,9,10,12-四氢-7H-色烯并[2,3-b]喹啉-3-醇}的毒理学和药理学评价、抗氧化作用、药物代谢动力学及药物毒性预测和分子模拟
Eur J Med Chem. 2014 Mar 3;74:491-501. doi: 10.1016/j.ejmech.2013.12.021. Epub 2014 Jan 8.
10
Topical pranoprofen 0.1% is as effective anti-inflammatory and analgesic agent as diclofenac sodium 0.1% after strabismus surgery.在斜视手术后，局部使用0.1%的普拉洛芬与使用0.1%的双氯芬酸钠一样，都是有效的抗炎和镇痛药。
J Ocul Pharmacol Ther. 2007 Jun;23(3):280-3. doi: 10.1089/jop.2006.108.