TY - JOUR
T1 - Exclusive regioselective 1,3-dipolar cycloaddition of 9-diazo-9H-fluorene and diphenyldiazomethane to 2-arylideneindane-1,3-diones
T2 - new approach toward effective synthesis of novel spiropyrazole derivatives
AU - Hussein, Essam M.
AU - Moussa, Ziad
AU - Ahmed, Saleh A.
N1 - Funding Information:
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.
Publisher Copyright:
© 2018, Springer-Verlag GmbH Austria, part of Springer Nature.
PY - 2018/11/1
Y1 - 2018/11/1
N2 - 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.].
AB - 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.].
KW - 1,3-Dipolar cycloaddition
KW - 9-Diazo-9H-fluorene
KW - DFT indices
KW - Diphenyldiazomethane
KW - HOMO–LUMO interaction
KW - Regioselectivity
KW - Spiropyrazoles
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U2 - 10.1007/s00706-018-2249-0
DO - 10.1007/s00706-018-2249-0
M3 - Article
AN - SCOPUS:85052948915
SN - 0026-9247
VL - 149
SP - 2021
EP - 2030
JO - Monatshefte fur Chemie
JF - Monatshefte fur Chemie
IS - 11
ER -