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Applying green and highly efficient approach for a facile synthesis of new thiazoloquinoline, thiazolopyridine, and thiazolonaphthyridine derivatives

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Abstract

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.

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Scheme 2

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Correspondence to Hamid Reza Shaterian.

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Arabpoor, Z., Shaterian, H.R. Applying green and highly efficient approach for a facile synthesis of new thiazoloquinoline, thiazolopyridine, and thiazolonaphthyridine derivatives. J IRAN CHEM SOC 16, 1091–1103 (2019). https://doi.org/10.1007/s13738-018-01579-x

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  • DOI: https://doi.org/10.1007/s13738-018-01579-x

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