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

Kiran, Kuppalli R. and Swaroop, Toreshettahally R. and Rajeev, Narasimhamurthy and Anil, Seegehalli M. and Rangappa, Kanchugarakoppal S. and Sadashiva, Maralinganadoddi P. (2020) Cyclization of Active Methylene Isocyanides with alpha-Oxodithioesters Induced by Base: An Expedient Synthesis of 4-Methylthio/Ethoxycarbonyl-5-acylthiazoles. Synthesis-Stuttgart, 52 (9). pp. 1444-1450. ISSN 1437-210X

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Abstract

Cyclization of tosylmethyl isocyanide with alpha-oxodithioesters in the presence of KOH is reported for the synthesis of 4-methylthio-5-acylthiazoles. Similarly, ethyl isocyanoacetate underwent cyclization with alpha-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.

Item Type: Article
Uncontrolled Keywords: thiazole; TosMIC; ethyl isocyanoacetate; alpha-oxodithioester; cyclization
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Mr Umendra uom
Date Deposited: 18 Feb 2021 09:32
Last Modified: 18 Feb 2021 09:32
URI: http://eprints.uni-mysore.ac.in/id/eprint/15588

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