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Synthesis 2017; 49(21): 4876-4886
DOI: 10.1055/s-0036-1590810
paper
© Georg Thieme Verlag Stuttgart · New York

Efficient One-Pot Synthesis of 2,4-Disubstituted Thiazoles and Dimeric Thiazoles Directly from Acyl Chlorides and β-Azido Disulfides

Yi Liu  *
a   School of Chemistry and Chemical Engineering, Yantai University, 30 Qingquan Rd, Laishan District, Yantai, 264005, P. R. of China   eMail: liuyi@ytu.edu.cn
,
Zhi Li
a   School of Chemistry and Chemical Engineering, Yantai University, 30 Qingquan Rd, Laishan District, Yantai, 264005, P. R. of China   eMail: liuyi@ytu.edu.cn
,
Yichuan Xie
a   School of Chemistry and Chemical Engineering, Yantai University, 30 Qingquan Rd, Laishan District, Yantai, 264005, P. R. of China   eMail: liuyi@ytu.edu.cn
,
Peng He
b   State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, P. R. of China   eMail: yuguodu@rcees.ac.cn
,
Junfei Qiao
b   State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, P. R. of China   eMail: yuguodu@rcees.ac.cn
,
Xinyuan Fan
c   Institute of Advanced Synthesis, Nanjing Tech University, Nanjing, 210009, P. R. of China
,
Yuguo Du*
b   State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, P. R. of China   eMail: yuguodu@rcees.ac.cn
› InstitutsangabenThis work was supported by the NNSFC projects (21402192, 21372254 and 21672255).
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Publikationsverlauf

Received: 26. April 2017

Accepted after revision: 31. Mai 2017

Publikationsdatum:
26. Juli 2017 (online)

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Abstract

A simple and effective one-pot cascade procedure to provide 2,4-disubstituted thiazoles and symmetrical dimeric thiazoles directly from commercially available acid chlorides and β-azido disulfides in moderate to high yields is described. This cascade transformation consists of disulfide cleavage, thiocarbonylation, phosphine-promoted intramolecular Staudinger/aza-Wittig reaction and dehydrogenation to form the corresponding thiazoles. The application of our methodology is demonstrated by the concise two-step synthesis of anticancer agent SMART and its O-linked dimer in 64% and 46% overall yields, respectively. This directed cascade reaction could be easily handled and scaled up under mild conditions, enabling the construction of focused thiazole derivatives for further pharmacological evaluation.

Key words

one-pot reaction - 2,4-disubstituted thiazole - dimeric thiazole - acid chloride - SMART

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590810.
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