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Synthesis 2017; 49(21): 4876-4886
DOI: 10.1055/s-0036-1590810
DOI: 10.1055/s-0036-1590810
paper
Efficient One-Pot Synthesis of 2,4-Disubstituted Thiazoles and Dimeric Thiazoles Directly from Acyl Chlorides and β-Azido Disulfides
Authors
This work was supported by the NNSFC projects (21402192, 21372254 and 21672255).
Weitere Informationen
Publikationsverlauf
Received: 26. April 2017
Accepted after revision: 31. Mai 2017
Publikationsdatum:
26. Juli 2017 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1590810.
- Supporting Information (PDF)
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For selected reviews, see: