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

  • Zahra Arabpoor
  • Hamid Reza ShaterianEmail author
Original Paper
  • 23 Downloads

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.

Graphical abstract

Keywords

Multi-component reaction Heterocycles Solvent-free Thiazoloquinoline Thiazolopyridine Thiazolonaphthyridine 

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Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of SciencesUniversity of Sistan and BaluchestanZahedanIran

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