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Molecular Diversity

, Volume 22, Issue 4, pp 907–917 | Cite as

Regioselective four-component synthesis of new tetrazolo[1,5-a]quinoline-based 2-amino-1,4-dihydropyridine and pyridin-2(1H)-one derivatives using nano-ZnO catalysis

  • Tooran Aghaalizadeh
  • Farough NasiriEmail author
Original Article
  • 87 Downloads

Abstract

Four-component reaction between primary amines, dialkylacetylendicarboxylates, tetrazolo[1,5-a] quinoline-4-carbaldehyde and ethyl-2-cyanoacetate in the presence of 1,4-diaza-bicyclo[2.2.2]octane and zinc oxide nanoparticles results to the regioselective production of new tetrazolo[1,5-a]quinoline-based 2-amino-1,4-dihydropyridine or pyridin-2(1H)-one derivatives in good to high yields. The selectivity of the catalyzed reaction toward the generation of the dihydropyridine or pyridin-2(1H)-one derivatives was found to be strongly dependent on the size of the alkyl groups in the ester moieties of the acetylenic esters. According to single-crystal X-ray diffraction and NMR studies, the pyridin-2(1H)-one derivatives involve a restricted rotation around the C–C bond connecting the tetrazoloquinoline and dihydropyridinone cyclic systems.

Graphical abstract

Keywords

Tetrazolo[15-a]quinoline-4-carbaldehyde Dialkylacetylendicarboxylate Ethyl-2-cyanoacetate Zinc oxide nanoparticles Enaminone Atropisomer MCRs 

Notes

Acknowledgements

The authors would like to express their appreciation for contributions of Professor Alireza Abbasi, Dr. Abolfazl Bezaatpour and Professor Nader Noroozi Pesyan to this work. Financial support of this research by University of Mohaghegh Ardabili, Iran, is gratefully acknowledged.

Supplementary material

11030_2018_9844_MOESM1_ESM.docx (3 mb)
Supplementary data (1H NMR and 13C NMR spectra for compounds 3a-3g and 4b, and 4h-4l) associated with this article can be found in the online version (DOCX 3105 kb)

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Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Applied ChemistryUniversity of Mohaghegh ArdabiliArdabilIran

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