Kiran, K. R. and Swaroop, T. R. and Rajeev, N. and Anil, S. M. and Rangappa, K. S. and Sadashiva, M. 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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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: | 07 Jul 2022 07:20 |
| URI: | http://eprints.uni-mysore.ac.in/id/eprint/15588 |
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