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苯乙酮肟中碳氢键与芳基乙酸和单质硫的官能团化反应

Functionalization of C-H bonds in acetophenone oximes with arylacetic acids and elemental sulfur.

作者信息

Pham Phuc H, Nguyen Khang X, Pham Hoai T B, Tran Thien T, Nguyen Tung T, Phan Nam T S

机构信息

Faculty of Chemical Engineering, Ho Chi Minh City University of Technology (HCMUT) 268 Ly Thuong Kiet, District 10 Ho Chi Minh City Vietnam

Vietnam National University Ho Chi Minh City Vietnam.

出版信息

RSC Adv. 2020 Mar 17;10(19):11024-11032. doi: 10.1039/d0ra00808g. eCollection 2020 Mar 16.

DOI:10.1039/d0ra00808g
PMID:35495317
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9050572/
Abstract

Fused thieno[3,2-]thiazoles were synthesized a coupling of acetophenone ketoximes, arylacetic acids, and elemental sulfur in the presence of LiCO base. Functionalities including chloro, bromo, fluoro, trifluoromethyl, and pyridyl groups were compatible with reaction conditions. High yields and excellent regioselectivities were obtained even if -substituted ketoxime acetates were used. Ethyl esters of heteroarylacetic acids were competent substrates, which is very rare in the literature. Our method would offer a convenient protocol to afford polyheterocyclic structures from simple substrates.

摘要

在碳酸锂碱存在下,通过苯乙酮肟、芳基乙酸和单质硫的偶联反应合成了稠合噻吩并[3,2 - ]噻唑。包括氯、溴、氟、三氟甲基和吡啶基在内的官能团与反应条件兼容。即使使用α - 取代的酮肟乙酸酯,也能获得高产率和优异的区域选择性。杂芳基乙酸乙酯是合适的底物,这在文献中非常罕见。我们的方法将提供一种从简单底物得到多杂环结构的便捷方案。

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RSC Adv. 2020 Mar 17;10(19):11024-11032. doi: 10.1039/d0ra00808g. eCollection 2020 Mar 16.
2
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本文引用的文献

1
Access to 2-Aroylthienothiazoles via C-H/N-O Bond Functionalization of Oximes.通过肟的C-H/N-O键官能化制备2-芳酰基噻吩并噻唑类化合物。
Org Lett. 2019 Dec 20;21(24):9976-9980. doi: 10.1021/acs.orglett.9b03900. Epub 2019 Dec 3.
2
Homo- and Heteroannulation of sp C-H Bonds in Acetophenones for Divergent Synthesis of Thienothiazoles.偕胺和杂环 sp C-H 键在苯乙酮中的环化反应用于噻吩并噻唑的多样性合成。
Org Lett. 2019 Nov 1;21(21):8795-8799. doi: 10.1021/acs.orglett.9b03414. Epub 2019 Oct 23.
3
Direct access to bis-S-heterocycles via copper-catalyzed three component tandem cyclization using S as a sulfur source.
通过铜催化的三组分串联环化反应,以 S 作为硫源,直接合成双-S-杂环化合物。
Org Biomol Chem. 2019 Mar 27;17(13):3424-3432. doi: 10.1039/c9ob00377k.
4
Branched-Selective Direct α-Alkylation of Cyclic Ketones with Simple Alkenes.支链选择性直接 α-烷基化环状酮与简单烯烃。
Angew Chem Int Ed Engl. 2019 Mar 22;58(13):4366-4370. doi: 10.1002/anie.201900301. Epub 2019 Feb 21.
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Ir(iii)-catalyzed C-H alkylations of (hetero)aromatic aldehydes using alkyl boron reagents.铱(iii)催化使用烷基硼试剂对(杂)芳族醛进行的C-H烷基化反应。
Chem Sci. 2018 Oct 3;9(48):8951-8956. doi: 10.1039/c8sc03606c. eCollection 2018 Dec 28.
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Sulfur-Promoted Decarboxylative Sulfurative Hexamerization of Phenylacetic Acids: Direct Approach to Hexabenzylidyne Tetrasulfides.硫促进的苯乙酸脱羧硫化六聚反应:直接合成六苄叉四硫化物的方法
Org Lett. 2019 Jan 4;21(1):279-282. doi: 10.1021/acs.orglett.8b03728. Epub 2018 Dec 14.
7
Thiophene-Fused Heteroaromatic Systems Enabled by Internal Oxidant-Induced Cascade Bis-Heteroannulation.噻吩稠合杂芳烃体系的内氧化剂诱导的串联双杂芳环化构建。
Org Lett. 2018 Aug 17;20(16):4917-4920. doi: 10.1021/acs.orglett.8b02049. Epub 2018 Aug 6.
8
Manganese-Catalyzed Redox-Neutral C-H Olefination of Ketones with Unactivated Alkenes.锰催化酮与未活化烯烃的氧化还原中性C-H烯基化反应
Angew Chem Int Ed Engl. 2018 Sep 10;57(37):12071-12075. doi: 10.1002/anie.201806287. Epub 2018 Aug 20.
9
Direct Observation of Radical Intermediates While Investigating the Redox Behavior of Thiamin Coenzyme Models.在研究硫胺素辅酶模型的氧化还原行为时对自由基中间体的直接观察
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Copper-catalyzed synthesis of thiazol-2-yl ethers from oxime acetates and xanthates under redox-neutral conditions.铜催化肟乙酸盐和黄原酸盐在氧化还原中性条件下合成噻唑-2-基醚。
Chem Commun (Camb). 2018 Apr 10;54(30):3767-3770. doi: 10.1039/c8cc00445e.