Halocyclization of Alkynoic Thioester and Oxidative Aromatization in One-Pot.
作者信息
Kurihara Miari, Shigehisa Hiroki
机构信息
Faculty of Pharmacy, Musashino University, 1-1-20 Shinmachi Nishitokyo, Tokyo 202-8585, Japan.
出版信息
J Org Chem. 2024 Jul 5;89(13):9700-9704. doi: 10.1021/acs.joc.4c01018. Epub 2024 Jun 14.
PMID:38875014
Abstract
This paper reports the halocyclization of alkynoic thioesters, as -nucleophiles, with -halosuccinimide, followed by oxidative aromatization with the same reagent for the one-pot synthesis of thiophenes, important heterocycles exhibiting remarkable applications in different disciplines. Brief mechanistic studies were also performed to elucidate the halocyclization process. The potential diverse applications of the product, dihydrothiophene, were also assessed.
摘要
相似文献
1
Halocyclization of Alkynoic Thioester and Oxidative Aromatization in One-Pot.
J Org Chem. 2024 Jul 5;89(13):9700-9704. doi: 10.1021/acs.joc.4c01018. Epub 2024 Jun 14.
2
Mechanistic Studies on Bromocyclization of Unsaturated Thioester by Density Functional Theory and Experiment.基于密度泛函理论和实验的不饱和硫酯溴环化反应机理研究
J Org Chem. 2024 May 17;89(10):7320-7323. doi: 10.1021/acs.joc.4c00477. Epub 2024 May 6.
3
Bromocyclization of Alkenoic Thioester and Access to Functionalized Sulfur-Heterocycles.链烯基硫酯的溴环化反应与功能化硫杂环化合物的合成
Org Lett. 2023 Dec 15;25(49):8777-8781. doi: 10.1021/acs.orglett.3c02953. Epub 2023 Oct 11.
4
Drug-S-acyl-glutathione thioesters: synthesis, bioanalytical properties, chemical reactivity, biological formation and degradation.药物-S-酰基-谷胱甘肽硫酯：合成、生物分析特性、化学反应性、生物形成和降解。
Curr Drug Metab. 2011 Mar;12(3):229-44. doi: 10.2174/138920011795101886.
5
Expanding the Reactivity of Flavin Dependent Halogenases Toward Olefins via Enantioselective Intramolecular Haloetherification and Chemoenzymatic Oxidative Rearrangements.通过对映选择性分子内卤醚化和化学酶促氧化重排扩展黄素依赖性卤化酶对烯烃的反应活性。
ACS Catal. 2022 Nov 4;12(21):13501-13505. doi: 10.1021/acscatal.2c03383. Epub 2022 Oct 20.
6
Enantioselective halocyclization of polyprenoids induced by nucleophilic phosphoramidites.亲核亚磷酰胺酯诱导的聚异戊二烯的对映选择性卤环化反应。
Nature. 2007 Feb 22;445(7130):900-3. doi: 10.1038/nature05553.
7
One-pot sequential multicomponent reaction between generated aldimines and succinaldehyde: facile synthesis of substituted pyrrole-3-carbaldehydes and applications towards medicinally important fused heterocycles.生成的醛亚胺与琥珀醛之间的一锅法顺序多组分反应：取代吡咯-3-甲醛的简便合成及其在重要药用稠合杂环化合物中的应用。
RSC Adv. 2018 Apr 24;8(28):15448-15458. doi: 10.1039/c8ra01637b. eCollection 2018 Apr 23.
8
Synthesis of Azonia Aromatic Heterocycles Bearing 6-6-6-5-6 Pentacyclic Core via Intramolecular [4 + 2]-Cycloaddition and Oxidative Aromatization Reaction Sequence in One Pot.通过分子内[4 + 2] - 环加成和氧化芳构化反应序列一锅法合成含6-6-6-5-6五环核心的氮杂芳族杂环化合物。
J Org Chem. 2024 Jan 5;89(1):68-79. doi: 10.1021/acs.joc.3c01506. Epub 2023 Dec 19.
9
A Cu(ii)-promoted tandem decarboxylative halogenation and oxidative diamination reaction of 2-aminopyridines with alkynoic acids for the synthesis of 2-haloimidazo[1,2-a]pyridines.一种铜（II）促进的2-氨基吡啶与炔酸的串联脱羧卤化和氧化双胺化反应，用于合成2-卤代咪唑并[1,2-a]吡啶。
Org Biomol Chem. 2017 Nov 15;15(44):9311-9318. doi: 10.1039/c7ob02014g.
10
Stereoselective halocyclization of alkenes with N-acyl hemiaminal nucleophiles.立体选择性环化烯烃与 N-酰基半亚胺亲核试剂。
Chirality. 2013 Nov;25(11):805-9. doi: 10.1002/chir.22219. Epub 2013 Aug 15.
引用本文的文献
1
Expedient Synthesis of Substituted Thieno[3,2-]thiophenes and Selenopheno[3,2-]selenophenes Through Cascade Cyclization of Alkynyl Diol Derivatives.通过炔二醇衍生物的级联环化反应便捷合成取代噻吩并[3,2-]噻吩和硒吩并[3,2-]硒吩
Molecules. 2024 Nov 21;29(23):5507. doi: 10.3390/molecules29235507.
Zotero 插件