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Natural deep eutectic solvents in the hetero-Diels-Alder approach to bis(indolyl)methanes

2019-07Journal article Restricted
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dc.contributor.authorGrosso, Carla
dc.contributor.authorBrigas, Amadeu
dc.contributor.authorde los Santos, Jesus M.
dc.contributor.authorPalacios, Francisco
dc.contributor.authorLemos, Americo
dc.contributor.authorPinho e Melo, Teresa M. V. D.
dc.date.accessioned2020-07-24T10:52:01Z
dc.date.available2020-07-24T10:52:01Z
dc.date.issued2019-07
dc.description.abstractFor the first time, the use of natural deep eutectic solvents (NADES) as reaction media to carry out hetero-Diels-Alder reactions is disclosed. This allowed to improve the efficiency and sustainability of the synthetic approach to bis(indolyl)methanes (BIMs) based on bis-hetero-Diels-Alder/conjugate addition reactions of nitroso- and azoalkenes with indoles. The ternary mixture of H2O with choline chloride/glycerol allowed the tuning of the physical properties of this NADES leading to a better solvent system, affording the target hydroxyiminomethyl- and hydrazonomethyl-BIMs, in much shorter reaction times, higher efficiency and easier isolation procedures. Furthermore, the direct access to carbonyl-BIMs was possible when 3-methyl-1-tert-butoxycarbonyl azoalkenes were used. [GRAPHICS] .
dc.description.sponsorshipPortuguese Agency for Scientific Research, Fundacao para a Ciencia e a Tecnologia (FCT) [UID/QUI/00313/2019]
dc.description.sponsorshipMinisterio de Economia, Industria y Competitividad (MINECO) [CTQ-2015-67871R]
dc.description.sponsorshipGobierno Vasco (GV)Basque Government [IT 992-16]
dc.description.sponsorshipFCTPortuguese Foundation for Science and Technology [SFRH/BD/130198/2017]
dc.description.versioninfo:eu-repo/semantics/publishedVersion
dc.identifier.doi10.1007/s00706-019-02421-7
dc.identifier.issn0026-9247
dc.identifier.issn1434-4475
dc.identifier.urihttp://hdl.handle.net/10400.1/14304
dc.language.isoeng
dc.peerreviewedyes
dc.publisherSpringer Wien
dc.relationSynthesis of Novel Indoles and Bisindolylmethanes: Approaches to Structures with Biological Activity
dc.subjectActive pharmaceutical ingredients
dc.subjectCatalytic asymmetric-synthesis
dc.subjectCarbonyl-compounds
dc.subjectVibrio-parahaemolyticus
dc.subjectIndole alkaloids
dc.subjectIonic liquids
dc.subjectOximes
dc.subjectNitrosoalkenes
dc.subjectDeoximation
dc.subjectMild
dc.titleNatural deep eutectic solvents in the hetero-Diels-Alder approach to bis(indolyl)methanes
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleSynthesis of Novel Indoles and Bisindolylmethanes: Approaches to Structures with Biological Activity
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBD%2F130198%2F2017/PT
oaire.citation.endPage1288
oaire.citation.issue7
oaire.citation.startPage1275
oaire.citation.titleMonatshefte für Chemie
oaire.citation.volume150
person.familyNameBrigas
person.familyNameLemos
person.givenNameAmadeu
person.givenNameAmerico
person.identifier.ciencia-idA81D-6DC7-31E4
person.identifier.orcid0000-0003-4875-4453
person.identifier.orcid0000-0001-9588-4555
person.identifier.ridE-1897-2012
person.identifier.ridB-4892-2008
person.identifier.scopus-author-id6701450565
person.identifier.scopus-author-id11139694000
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsrestrictedAccess
rcaap.typearticle
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relation.isAuthorOfPublication70dfe028-027a-4dec-b6e3-1a49c9be9e60
relation.isAuthorOfPublication.latestForDiscovery7b0e903c-4730-497c-a012-f9fa0fc5e6dc
relation.isProjectOfPublication5266e991-cce6-4ddd-bea9-308a711ef78a
relation.isProjectOfPublication.latestForDiscovery5266e991-cce6-4ddd-bea9-308a711ef78a

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