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Molecular Diversity

, Volume 22, Issue 4, pp 969–977 | Cite as

An efficient and facile synthesis of new tetracyclic fused pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones

  • Mohsen A.-M. GomaaEmail author
  • Huda A. Ali
Original Article
  • 286 Downloads

Abstract

Reaction of amidrazones 1a–1i with (1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile (2) in ethyl acetate solution in one-step reaction led to the formation of unprecedented pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones 3a–3g along with pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-12b-oles 3h–3m in moderate to excellent yields. These novel heterocycles were formed via a Michael addition reaction followed by intramolecular cyclization via a dearomatization process.

Keywords

Pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolone Amidrazone (1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile Dearomatization 

Notes

Acknowledgements

We are grateful to Prof. Dr. Jens Christoffers at Institut für Chemie Carl von Ossietzky Universität Oldenburg and Prof. Dr. Georg Manolikakes Fachbereich Chemie-Organische Chemie TU Kaiserslautern for kind help in the measurements of some NMR spectra and HRMS experiments.

Supplementary material

11030_2018_9849_MOESM1_ESM.docx (990 kb)
Supplementary material 1 (DOCX 989 kb)

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Copyright information

© Springer International Publishing AG, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceMinia UniversityEl-MiniaEgypt

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