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-diazaspiro[4.4]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.
Experimental and theoretical DFT investigations in the [2, 3]-wittig-type rearrangement of propargyl/allyl-oxy-pyrazolones
Ciancaleoni G.;Costamagna M.;
2021-01-01
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-diazaspiro[4.4]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.File in questo prodotto:
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