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苯乙酮向咪唑硫酮的均相缩合反应。

Homo-condensation of acetophenones toward imidazothiones.

作者信息

Pham Phuc Hoang, Thien Nguyen Phuc Thai, Bui Thuy Thu, Tra Hien Nhat, Nguyen Tung Thanh, Son Phan Nam Thanh

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 Linh Trung Ward, Thu Duc District Ho Chi Minh City Vietnam.

出版信息

RSC Adv. 2020 Nov 4;10(66):40225-40228. doi: 10.1039/d0ra03047c. eCollection 2020 Nov 2.

DOI:10.1039/d0ra03047c
PMID:35520859
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9057481/
Abstract

Direct synthesis of imidazothiones from simple, commercial substrates is not known. We report a method for the condensation of acetophenones, elemental sulfur, and ammonium acetate as a nitrogen source to obtain the hitherto challenging five-membered heterocycles. Functionalities such as halogen, trifluoromethyl, cyano, methylthio, and heteroaryl groups were well tolerated.

摘要

目前尚不知道能否从简单的商业底物直接合成咪唑硫酮。我们报道了一种方法,该方法利用苯乙酮、元素硫和作为氮源的醋酸铵进行缩合反应,以获得迄今为止颇具挑战性的五元杂环化合物。卤素、三氟甲基、氰基、甲硫基和杂芳基等官能团具有良好的耐受性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82ba/9057481/fa821d5b79ba/d0ra03047c-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82ba/9057481/2e1aeb43717c/d0ra03047c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82ba/9057481/576b256d5073/d0ra03047c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82ba/9057481/61a98cc250c5/d0ra03047c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82ba/9057481/af433d8a0247/d0ra03047c-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82ba/9057481/fa821d5b79ba/d0ra03047c-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82ba/9057481/2e1aeb43717c/d0ra03047c-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82ba/9057481/576b256d5073/d0ra03047c-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82ba/9057481/61a98cc250c5/d0ra03047c-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82ba/9057481/af433d8a0247/d0ra03047c-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/82ba/9057481/fa821d5b79ba/d0ra03047c-s5.jpg

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本文引用的文献

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Org Lett. 2019 Dec 20;21(24):9976-9980. doi: 10.1021/acs.orglett.9b03900. Epub 2019 Dec 3.
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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.
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镍(ii)催化的 C(sp)-H 硫化/环化反应与元素硫:选择性合成苯并异噻唑酮。
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Base-Controlled Three Component Reactions of Amines, Elemental Sulfur, and Styrenes: Synthesis of Thioamides under Metal-Free Conditions.碱催化的胺、单质硫和苯乙烯的三组分反应:无金属条件下硫代酰胺的合成
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