Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones

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 nucle...

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Autores principales: Crescentini, Lucia De, Favi, Gianfranco, Mari, Giacomo, Ciancaleoni, Gianluca, Costamagna, Marcello, Santeusanio, Stefania, Mantellini, Fabio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
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Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8587800/
https://www.ncbi.nlm.nih.gov/pubmed/34770965
http://dx.doi.org/10.3390/molecules26216557
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author Crescentini, Lucia De
Favi, Gianfranco
Mari, Giacomo
Ciancaleoni, Gianluca
Costamagna, Marcello
Santeusanio, Stefania
Mantellini, Fabio
author_facet Crescentini, Lucia De
Favi, Gianfranco
Mari, Giacomo
Ciancaleoni, Gianluca
Costamagna, Marcello
Santeusanio, Stefania
Mantellini, Fabio
author_sort Crescentini, Lucia De
collection PubMed
description 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.
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spelling pubmed-85878002021-11-13 Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones Crescentini, Lucia De Favi, Gianfranco Mari, Giacomo Ciancaleoni, Gianluca Costamagna, Marcello Santeusanio, Stefania Mantellini, Fabio Molecules Article 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. MDPI 2021-10-29 /pmc/articles/PMC8587800/ /pubmed/34770965 http://dx.doi.org/10.3390/molecules26216557 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Crescentini, Lucia De
Favi, Gianfranco
Mari, Giacomo
Ciancaleoni, Gianluca
Costamagna, Marcello
Santeusanio, Stefania
Mantellini, Fabio
Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones
title Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones
title_full Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones
title_fullStr Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones
title_full_unstemmed Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones
title_short Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones
title_sort experimental and theoretical dft investigations in the [2,3]-wittig-type rearrangement of propargyl/allyl-oxy-pyrazolones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8587800/
https://www.ncbi.nlm.nih.gov/pubmed/34770965
http://dx.doi.org/10.3390/molecules26216557
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