Applying green and highly efficient approach for a facile synthesis of new thiazoloquinoline, thiazolopyridine, and thiazolonaphthyridine derivatives
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An eco-friendly approach for the synthesis of new thiazoloquinolines, thiazolopyridines, and thiazolonaphthyridines scaffolds has been achieved using α-enolicdithioesters, cysteamine, arylglyoxal monohydrate, and cyclic 1,3-diketones (dimedone, 4-hydroxycoumarin, and 4-hydroxy-1-methyl-2(1H)-quinolone) under thermal solvent-free conditions. The highlight of this protocol is the generation of two heterocyclic rings, using a domino, one-pot, four-component reaction. In producing heterocyclic rings first, a thiazole ring generated from the reaction of α-enolicdithioesters and cysteamine is achieved. Second heterocyclic ring formed by the condensation of conjugated thiazole with the Knoevenagel product achieved from arylglyoxal monohydrate and 1,3-diketones followed by an N-cyclization. Catalyst- and solvent-free, short reaction times, high yields and a simple work-up make it an attractive protocol for the preparation of diversified thiazoloquinoline, thiazolopyridine, and thiazolonaphthyridine derivatives.
KeywordsMulti-component reaction Heterocycles Solvent-free Thiazoloquinoline Thiazolopyridine Thiazolonaphthyridine
- 14.A.A. Altaf, A. Shahzad, Z. Gul, N. Rasool, A. Badshah, B. Lal, E. Khan, JDDMC 1, 1 (2015)Google Scholar