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通过三组分反应一锅法合成1,3,5-三嗪-2,4-二硫酮衍生物

One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions.

作者信息

Kang Gui-Feng, Zhang Gang

机构信息

School of Pharmaceutical Sciences, Capital Medical University, Beijing 100069, China.

State Key Laboratory of Bioactive Substances and Function of Natural Medicine, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China.

出版信息

Beilstein J Org Chem. 2020 Jun 24;16:1447-1455. doi: 10.3762/bjoc.16.120. eCollection 2020.

DOI:10.3762/bjoc.16.120
PMID:32647546
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7323627/
Abstract

A catalyst-free one-pot synthetic methodology was developed for the preparation of 1,3,5-triazine-2,4-dithione derivatives through three-component reactions of arylaldehydes, thiourea, and orthoformates. The procedure tolerated a diverse range of arylaldehydes and orthoformates and provided a rapid entry to a variety of 4-aryl-6-(alkylthio)-3,4-dihydro-1,3,5-triazine-2(1)-thiones (29 examples). The synthetic strategy relies on the dual role of thiourea in the cyclization with the aldehydes and the alkylation via an intermediate imidate formation. The structures of 1,3,5-triazine-2,4-dithione derivatives were characterized by spectroscopic techniques as well as by single crystal X-ray diffraction.

摘要

开发了一种无催化剂的一锅合成方法，用于通过芳醛、硫脲和原甲酸酯的三组分反应制备1,3,5-三嗪-2,4-二硫酮衍生物。该方法耐受多种芳醛和原甲酸酯，并能快速合成多种4-芳基-6-(烷硫基)-3,4-二氢-1,3,5-三嗪-2(1)-硫酮（29个实例）。该合成策略依赖于硫脲在与醛环化以及通过中间体亚胺酯形成进行烷基化过程中的双重作用。1,3,5-三嗪-2,4-二硫酮衍生物的结构通过光谱技术以及单晶X射线衍射进行了表征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/0245d57acb35/Beilstein_J_Org_Chem-16-1447-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/85c03d82105b/Beilstein_J_Org_Chem-16-1447-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/f82958042052/Beilstein_J_Org_Chem-16-1447-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/5e4094db768e/Beilstein_J_Org_Chem-16-1447-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/b3776a573928/Beilstein_J_Org_Chem-16-1447-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/b38f21c3e463/Beilstein_J_Org_Chem-16-1447-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/28a90b6a3359/Beilstein_J_Org_Chem-16-1447-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/25a91dc02148/Beilstein_J_Org_Chem-16-1447-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/0245d57acb35/Beilstein_J_Org_Chem-16-1447-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/85c03d82105b/Beilstein_J_Org_Chem-16-1447-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/f82958042052/Beilstein_J_Org_Chem-16-1447-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/5e4094db768e/Beilstein_J_Org_Chem-16-1447-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/b3776a573928/Beilstein_J_Org_Chem-16-1447-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/b38f21c3e463/Beilstein_J_Org_Chem-16-1447-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/28a90b6a3359/Beilstein_J_Org_Chem-16-1447-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/25a91dc02148/Beilstein_J_Org_Chem-16-1447-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/0937/7323627/0245d57acb35/Beilstein_J_Org_Chem-16-1447-g009.jpg

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