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)1<i>H</i>-pyrazol-5(4<i>H</i>)-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...

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Autores principales:	Lucia De Crescentini, Gianfranco Favi, Giacomo Mari, Gianluca Ciancaleoni, Marcello Costamagna, Stefania Santeusanio, Fabio Mantellini
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	[2,3]-Wittig rearrangement pyrazolones propargyl alcohol allyl alcohol 1,2-diaza-,1,3-dienes DFT study Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/c11df27f83ad4d3399334d012181b3a2
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spelling	oai:doaj.org-article:c11df27f83ad4d3399334d012181b3a22021-11-11T18:32:27ZExperimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones10.3390/molecules262165571420-3049https://doaj.org/article/c11df27f83ad4d3399334d012181b3a22021-10-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/21/6557https://doaj.org/toc/1420-3049Here we report the synthesis of interesting 3-alkyl-4-hydroxy-1-aryl-4-(propa-1,2-dienyl)1<i>H</i>-pyrazol-5(4<i>H</i>)-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-1<i>H</i>-pyrazol-5(4<i>H</i>)-ones. A DFT study was also carried out, in order to have decisive clarifications about the mechanism.Lucia De CrescentiniGianfranco FaviGiacomo MariGianluca CiancaleoniMarcello CostamagnaStefania SanteusanioFabio MantelliniMDPI AGarticle[2,3]-Wittig rearrangementpyrazolonespropargyl alcoholallyl alcohol1,2-diaza-,1,3-dienesDFT studyOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6557, p 6557 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	[2,3]-Wittig rearrangement pyrazolones propargyl alcohol allyl alcohol 1,2-diaza-,1,3-dienes DFT study Organic chemistry QD241-441
spellingShingle	[2,3]-Wittig rearrangement pyrazolones propargyl alcohol allyl alcohol 1,2-diaza-,1,3-dienes DFT study Organic chemistry QD241-441 Lucia De Crescentini Gianfranco Favi Giacomo Mari Gianluca Ciancaleoni Marcello Costamagna Stefania Santeusanio Fabio Mantellini Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones
description	Here we report the synthesis of interesting 3-alkyl-4-hydroxy-1-aryl-4-(propa-1,2-dienyl)1<i>H</i>-pyrazol-5(4<i>H</i>)-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-1<i>H</i>-pyrazol-5(4<i>H</i>)-ones. A DFT study was also carried out, in order to have decisive clarifications about the mechanism.
format	article
author	Lucia De Crescentini Gianfranco Favi Giacomo Mari Gianluca Ciancaleoni Marcello Costamagna Stefania Santeusanio Fabio Mantellini
author_facet	Lucia De Crescentini Gianfranco Favi Giacomo Mari Gianluca Ciancaleoni Marcello Costamagna Stefania Santeusanio Fabio Mantellini
author_sort	Lucia De Crescentini
title	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_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_sort	experimental and theoretical dft investigations in the [2,3]-wittig-type rearrangement of propargyl/allyl-oxy-pyrazolones
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/c11df27f83ad4d3399334d012181b3a2
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Experimental and Theoretical DFT Investigations in the [2,3]-Wittig-Type Rearrangement of Propargyl/Allyl-Oxy-Pyrazolones

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