Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones |
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| Authors: | Lucia De Crescentini Gianfranco Favi Giacomo Mari Gianluca Ciancaleoni Marcello Costamagna Stefania Santeusanio Fabio Mantellini |
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| Institution: | 1.Department of Biomolecular Sciences, Section of Organic Chemistry and Organic Natural Compounds, University of Urbino “Carlo Bo”, Via I Maggetti 24, 61029 Urbino, PU, Italy; (G.F.); (G.M.); (S.S.);2.Department of Chemistry and Industrial Chemistry, University of Pisa, Via G. Moruzzi 13, 56124 Pisa, PI, Italy; (G.C.); (M.C.) |
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| Abstract: | Here we report the synthesis of interesting 3-alkyl-4-hydroxy-1-aryl-4-(propa-1,2-dienyl)1H-pyrazol-5(4H)-ones and 9-alkyl-7-aryl-1-oxa-7,8-diazaspiro4.4]nona-3,8-dien-6-ones, starting from 1,2-diaza-1,3-dienes (DDs) and propargyl alcohol. The reaction proceeds through a sequence Michael-type nucleophilic attack/cyclization/2,3]-Wittig rearrangement. In the same way, the reaction between the aforementioned DDs and allyl alcohol furnished 4-allyl-4-hydroxy-3-alkyl-1-aryl-1H-pyrazol-5(4H)-ones. A DFT study was also carried out, in order to have decisive clarifications about the mechanism. |
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| Keywords: | [2 3]-Wittig rearrangement pyrazolones propargyl alcohol allyl alcohol 1 2-diaza- 1 3-dienes DFT study |
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