Cyclization of Active Methylene Isocyanides with α-Oxodithioesters Induced by Base: An Expedient Synthesis of 4-Methylthio/Ethoxycarbonyl-5-acylthiazoles

Autor:	Maralinganadoddi P. Sadashiva, Kuppalli R Kiran, Toreshettahally R. Swaroop, Seegehalli M Anil, Narasimhamurthy Rajeev, Kanchugarakoppal S. Rangappa
Rok vydání:	2020
Předmět:	chemistry.chemical_classification Base (chemistry) 010405 organic chemistry Organic Chemistry TosMIC 010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound chemistry Tosylmethyl isocyanide Methylene Thiazole
Zdroj:	Synthesis. 52:1444-1450
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0039-1690821
Popis:	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.
Databáze:	OpenAIRE
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