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Synthesis 2020; 52(09): 1444-1450
DOI: 10.1055/s-0039-1690821
DOI: 10.1055/s-0039-1690821
paper
Cyclization of Active Methylene Isocyanides with α-Oxodithioesters Induced by Base: An Expedient Synthesis of 4-Methylthio/Ethoxycarbonyl-5-acylthiazoles
The authors are grateful to UGC-SAP DRS III for providing financial support and IOE for instrumentation facility.Further Information
Publication History
Received: 10 January 2020
Accepted after revision: 23 January 2020
Publication Date:
17 February 2020 (online)
Abstract
Cyclization of tosylmethyl isocyanide with α-oxodithioesters in the presence of KOH is reported for the synthesis of 4-methylthio-5-acylthiazoles. Similarly, ethyl isocyanoacetate underwent cyclization with α-oxodithioesters to form 4-ethoxycarbonyl-5-acylthiazoles in the presence of DBU/EtOH. Mechanisms for the formation of thiazoles are proposed. These thiazoles can also be obtained by Takeda reaction, in which thiazole-4,5-anhydride is acylated with aromatic compounds followed by esterification; however, that approach requires two steps and suffers from the formation of a regioisomeric mixture of products.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690821.
- Supporting Information
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