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Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 11, pp 2021–2030 | Cite as

Exclusive regioselective 1,3-dipolar cycloaddition of 9-diazo-9H-fluorene and diphenyldiazomethane to 2-arylideneindane-1,3-diones: new approach toward effective synthesis of novel spiropyrazole derivatives

  • Essam M. Hussein
  • Ziad Moussa
  • Saleh A. Ahmed
Original Paper
  • 86 Downloads

Abstract

A simple, convenient, and regioselective 1,3-dipolar cycloaddition of 9-diazo-9H-fluorene or diphenyldiazomethane to 2-arylidene-1H-indene-1,3(2H)-diones afforded a series of novel dispiro[indane-2,3′-pyrazole-5′,9″-fluorene] and spiro[indene-2,3′-pyrazole] derivatives in moderate to excellent yields. Chemical structures of all products have been fully established by 1D (1H, 13C, 13C-DEPT 90) and 2D homonuclear and heteronuclear correlation NMR spectrometry experiments (1H-1H-DQF-COSY, 1H-1H-TOCSY, 13C-1H-HSQC, 13C-1H-HMBC, 1H-1H ROESY, and HSQC-TOCSY) and regioselectivity of the reported procedure has been demonstrated in all products. DFT reactivity indices of these cycloaddition reactions have been studied. 1,3-Dipolar cycloaddition of 9-diazo-9H-fluorene and diphenyldiazomethane to 2-arylidene-1H-indene-1,3(2H)-diones as dipolarophiles are reactions governed by a concerted mechanism exhibiting high regioselectivity.

Graphical abstract

Keywords

1,3-Dipolar cycloaddition 9-Diazo-9H-fluorene Diphenyldiazomethane Spiropyrazoles Regioselectivity DFT indices HOMO–LUMO interaction 

Notes

Acknowledgements

S. A. Ahmed is highly indebted to Alexander von Humboldt Foundation (AvH) and Prof. Jochen Mattay, Bielefeld University, Germany for helping with some analytical and spectroscopic measurements in addition to some labware donations.

Supplementary material

706_2018_2249_MOESM1_ESM.pdf (2.5 mb)
Supplementary material 1 (PDF 2610 kb)

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  • Essam M. Hussein
    • 1
    • 2
  • Ziad Moussa
    • 3
  • Saleh A. Ahmed
    • 1
    • 2
  1. 1.Chemistry Department, Faculty of Applied ScienceUmm Al-Qura UniversityMakkahSaudi Arabia
  2. 2.Chemistry Department, Faculty of ScienceAssiut UniversityAssiutEgypt
  3. 3.Department of Chemistry, Faculty of ScienceTaibah UniversityAlmadinah AlmunawarrahSaudi Arabia

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