Tetrahedron p. 5617 - 5640 (1997)
Update date:2022-08-05
Topics:
Attanasi, Orazio A.
De Crescentini, Lucia
Filippone, Paolino
Foresti, Elisabetta
Galeazzi, Roberta
Ghiviriga, Ion
Katritzky, Alan R.
1-Substituted 4-alkoxy-, 4-alkylthio-, and 4-aryloxy-1H-pyrazol-5(2H)-ones have been prepared by the reaction of conjugated azoalkenes with alcohols, thiols, and phenols. In some cases the intermediate hydrazones were isolated, while in others the products were obtained in one step. 1-Unsubstituted 4-alkoxy-, 4-alkylthio-, and 4-aryloxy-1H-pyrazol-5(2H)-ones were produced by methanolysis of the corresponding 1-substituted derivatives under reflux. Some of these compounds were studied by molecular mechanics calculations, as well as deuterium induced shifts (DIS) on 13C chemical shifts, and tentative conclusion was drawn about their tautomerism and conformations. X-Ray crystal structure determinations of 1-(aminocarbonyl)-3-methyl- 4-methoxy-1H-pyrazol-5(2H)-one 4e and 3-methyl-4-methoxy-1H-pyrazol-5(2H)-one 5a demonstrated that both molecules exist in the crystal exclusively in the HN-CO tautomeric form. Some previously reported structural assignments in some pyrazolones and hydroxypyrazoles were corrected.
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Doi:10.1016/S0040-4039(97)00732-6
(1997)Doi:10.1039/jr9650005920
(1965)Doi:10.1002/cber.19971300610
(1997)Doi:10.1055/s-2008-1067096
(2008)Doi:10.1016/S0040-4039(97)00927-1
(1997)Doi:10.1016/S0022-328X(96)06587-4
(1997)