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 - 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 -