Combination of multicomponent KA2 and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones

The Cu-catalyzed multicomponent ketone–amine–alkyne (KA2) reaction was combined with a Pauson–Khand cycloaddition to give access of unprecedented constrained spirocyclic pyrrolocyclopentenone derivatives following a DOS couple-pair approach. The polyfunctional molecular scaffolds were tested on the...

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Main Authors:	Riccardo Innocenti, Elena Lenci, Gloria Menchi, Andrea Trabocchi
Format:	Article
Language:	English
Published:	Beilstein-Institut 2020-02-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	chemical libraries chemoinformatics cu-catalysis cycloadditions molecular scaffolds multicomponent reactions
Online Access:	https://doi.org/10.3762/bjoc.16.23

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spelling	doaj-0aa7afa4c3e1487491a29a93936e3d222021-03-02T07:53:03ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-02-0116120021110.3762/bjoc.16.231860-5397-16-23Combination of multicomponent KA2 and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenonesRiccardo Innocenti0Elena Lenci1Gloria Menchi2Andrea Trabocchi3Department of Chemistry “Ugo Schiff”, University of Florence, Via della Lastruccia 13, 50019 Sesto Fiorentino, Florence, Italy,Department of Chemistry “Ugo Schiff”, University of Florence, Via della Lastruccia 13, 50019 Sesto Fiorentino, Florence, Italy,Department of Chemistry “Ugo Schiff”, University of Florence, Via della Lastruccia 13, 50019 Sesto Fiorentino, Florence, Italy,Department of Chemistry “Ugo Schiff”, University of Florence, Via della Lastruccia 13, 50019 Sesto Fiorentino, Florence, Italy,The Cu-catalyzed multicomponent ketone–amine–alkyne (KA2) reaction was combined with a Pauson–Khand cycloaddition to give access of unprecedented constrained spirocyclic pyrrolocyclopentenone derivatives following a DOS couple-pair approach. The polyfunctional molecular scaffolds were tested on the cyclopentenone reactivity to further expand the skeletal diversity, demonstrating the utility of this combined approach in generating novel spiro compounds as starting material for the generation of chemical libraries. The chemoinformatics characterization of the newly-synthesized molecules gave evidence about structural and physicochemical properties with respect to a set of blockbuster drugs, and showed that such scaffolds are drug-like but more spherical and three-dimensional in character than the drugs.https://doi.org/10.3762/bjoc.16.23chemical librarieschemoinformaticscu-catalysiscycloadditionsmolecular scaffoldsmulticomponent reactions
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Riccardo Innocenti Elena Lenci Gloria Menchi Andrea Trabocchi
spellingShingle	Riccardo Innocenti Elena Lenci Gloria Menchi Andrea Trabocchi Combination of multicomponent KA2 and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones Beilstein Journal of Organic Chemistry chemical libraries chemoinformatics cu-catalysis cycloadditions molecular scaffolds multicomponent reactions
author_facet	Riccardo Innocenti Elena Lenci Gloria Menchi Andrea Trabocchi
author_sort	Riccardo Innocenti
title	Combination of multicomponent KA2 and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones
title_short	Combination of multicomponent KA2 and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones
title_full	Combination of multicomponent KA2 and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones
title_fullStr	Combination of multicomponent KA2 and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones
title_full_unstemmed	Combination of multicomponent KA2 and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones
title_sort	combination of multicomponent ka2 and pauson–khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2020-02-01
description	The Cu-catalyzed multicomponent ketone–amine–alkyne (KA2) reaction was combined with a Pauson–Khand cycloaddition to give access of unprecedented constrained spirocyclic pyrrolocyclopentenone derivatives following a DOS couple-pair approach. The polyfunctional molecular scaffolds were tested on the cyclopentenone reactivity to further expand the skeletal diversity, demonstrating the utility of this combined approach in generating novel spiro compounds as starting material for the generation of chemical libraries. The chemoinformatics characterization of the newly-synthesized molecules gave evidence about structural and physicochemical properties with respect to a set of blockbuster drugs, and showed that such scaffolds are drug-like but more spherical and three-dimensional in character than the drugs.
topic	chemical libraries chemoinformatics cu-catalysis cycloadditions molecular scaffolds multicomponent reactions
url	https://doi.org/10.3762/bjoc.16.23
work_keys_str_mv	AT riccardoinnocenti combinationofmulticomponentka2andpausonkhandreactionsshortsynthesisofspirocyclicpyrrolocyclopentenones AT elenalenci combinationofmulticomponentka2andpausonkhandreactionsshortsynthesisofspirocyclicpyrrolocyclopentenones AT gloriamenchi combinationofmulticomponentka2andpausonkhandreactionsshortsynthesisofspirocyclicpyrrolocyclopentenones AT andreatrabocchi combinationofmulticomponentka2andpausonkhandreactionsshortsynthesisofspirocyclicpyrrolocyclopentenones
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Combination of multicomponent KA2 and Pauson–Khand reactions: short synthesis of spirocyclic pyrrolocyclopentenones

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