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

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

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: [Figure not available: see fulltext.].

Original languageEnglish
Pages (from-to)2021-2030
Number of pages10
JournalMonatshefte fur Chemie
Volume149
Issue number11
DOIs
Publication statusPublished - Nov 1 2018
Externally publishedYes

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

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