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One-pot pseudo three-component condensation reaction of arylglyoxal monohydrates with 1-ethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione for the synthesis of new pyrano[2,3-d:6,5-d’]dipyrimidines as HIV integrase inhibitor-like frameworks using two different environmentally benign catalytic systems

  • Mehdi RimazEmail author
  • Hossein Mousavi
  • Behzad Khalili
  • Leila Sarvari
Original Paper
  • 23 Downloads

Abstract

Simple, selective and highly efficient one-pot synthesis of new 5-aryloyl-1,9-diethyl-2,8-dithioxo-2,3,5,7,8,9-hexahydro-4H-pyrano[2,3-d:6,5-d’]dipyrimidine-4,6(1H)-dione derivatives has been developed using pseudo three-component reaction of arylglyoxal monohydrates with 1-ethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione in the presence of a catalytic amount of 1,4-diazabicyclo[2.2.2]octane (DABCO) or ZrOCl2.8H2O as green catalysts in ethanol at 50 °C. The significant features of the present work are simplicity, regio- and chemoselectivity, short reaction times, good to excellent yields, avoiding the use of any hazardous catalyst or solvent, and easy work-up procedure. The structures of the compounds were confirmed by FT-IR, 1H NMR, and 13C NMR spectroscopy data and also microanalysis. The synthetic strategies reported herein can be also regarded as green and efficient methods for the preparation of some HIV integrase inhibitor-like compounds especially new V-165 analogs.

Graphical Abstract

Keywords

Pyranodipyrimidine Arylglyoxal monohydrate Green chemistry DABCO ZrOCl2.8H2

Notes

Acknowledgements

Financial supports from the Research Council of Payame Noor University (Grant 68424) is gratefully acknowledged.

Supplementary material

13738_2019_1642_MOESM1_ESM.doc (3.5 mb)
Supplementary material 1 (DOC 3 KB)

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Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  1. 1.Department of ChemistryPayame Noor UniversityTehranIran
  2. 2.Department of Chemistry, Faculty of SciencesUniversity of GuilanRashtIran

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