| Title: |
Base-promoted regioselective synthesis of alkyl (2-tosyl/4-ethylcarbonyl) thiazole-5-carboxylates employing dithioates and active methylene isocyanides. |
| Authors: |
Santhosh, Chikkappaiahnayaka1 (AUTHOR), Singh, Krishna Ravi1 (AUTHOR), Mane, Manoj V.2 (AUTHOR), Sheela, Kalleshappa1 (AUTHOR), Sharath, Kalleshappa1 (AUTHOR), Sadashiva, Maralinganadoddi P.1 (AUTHOR) mpsadashiva@gmail.com |
| Source: |
New Journal of Chemistry. 3/21/2025, Vol. 49 Issue 11, p4604-4614. 11p. |
| Subject Terms: |
*REGIOSELECTIVITY (Chemistry), *ISOCYANIDES, *X-ray diffraction, *FUNCTIONAL groups, *RING formation (Chemistry) |
| Abstract: |
Herein, we report highly efficient and base-promoted approaches for the diversity-oriented synthesis of 2,5- and 4,5-disubstituted thiazoles using alkyl 2-(methylthio)-2-thioxoacetates as synthetic precursors. The transformation involves the regioselective cyclization reaction between dithioates and active methylene isocyanides, leading to the tosyl and ester-substituted thiazoles at the 2nd and 4th positions, respectively. Notably, the reactions occur rapidly at room temperature under metal-free mild conditions, highlighting the practical applicability of this protocol. The methodology exhibits broad functional group compatibility at the 5th position of the thiazole, accompanied by excellent yields, providing a valuable alternative to existing synthetic routes. The regioselective cyclized products were characterized and confirmed through single-crystal X-ray diffraction studies. Furthermore, it enriches the DFT-mechanistic studies for selective cyclization. [ABSTRACT FROM AUTHOR] |
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| Database: |
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