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dc.contributor.author
Martins, Guilherme A. M.
dc.contributor.author
Carmo, Gabriele do
dc.contributor.author
Morel, Ademir F.
dc.contributor.author
Kaufman, Teodoro Saul
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dc.contributor.author
Silveira, Claudio C.
dc.date.available
2020-05-08T15:25:00Z
dc.date.issued
2019-01
dc.identifier.citation
Martins, Guilherme A. M.; Carmo, Gabriele do; Morel, Ademir F.; Kaufman, Teodoro Saul; Silveira, Claudio C.; A Convenient and Atom-Economic One-Pot Selenium-Chloride-Mediated Synthesis of 2-Arylselenopheno[2,3-b] indoles and Their Antifungal Activity; Wiley-VCH; Asian Journal of Organic Chemistry; 8; 3; 1-2019; 369-375
dc.identifier.issn
2193-5807
dc.identifier.uri
http://hdl.handle.net/11336/104624
dc.description.abstract
A facile and convenient atom‐economic protocol for the one‐pot synthesis of 2‐aryl selenopheno[2,3‐b]indoles, by an electrophilic cyclization of 3‐(arylalkynyl)indoles with SeCl2 prepared in situ as the selenium source, is reported. The tricyclic products were obtained in moderate to very good yields. The reaction was optimized, and its scope and limitations were systematically studied. It was observed that its performance was affected by the steric and electronic properties of the substituent attached to the nitrogen atom and to a lesser extent by the nature and position of the substituents of the pending aryl moiety. Halogen atoms located para to the alkynyl group caused an average of 20% yield reduction. The reaction was unsuccessful with substrates bearing an alkyl chain attached to one of the sides of the alkynyl moiety. The antifungal activity of selected tricyclic compounds was tested against a panel of clinically relevant yeasts, and one of the heterocycles was exceptionally effective against Cryptococcus neoformans and C. gatti.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Wiley-VCH
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dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.subject
CYCLIZATION OF HETEROCYCLES
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SELENIUM DERIVATIVES
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ALKYNES
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ANTIFUNGAL AGENTS
dc.subject.classification
Química Orgánica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
A Convenient and Atom-Economic One-Pot Selenium-Chloride-Mediated Synthesis of 2-Arylselenopheno[2,3-b] indoles and Their Antifungal Activity
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2020-05-04T20:58:44Z
dc.identifier.eissn
2193-5807
dc.journal.volume
8
dc.journal.number
3
dc.journal.pagination
369-375
dc.journal.pais
Estados Unidos
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dc.journal.ciudad
Nueva York
dc.description.fil
Fil: Martins, Guilherme A. M.. Universidade Federal de Santa Maria.; Brasil
dc.description.fil
Fil: Carmo, Gabriele do. Universidade Federal de Santa Maria.; Brasil
dc.description.fil
Fil: Morel, Ademir F.. Universidade Federal de Santa Maria.; Brasil
dc.description.fil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
dc.description.fil
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria.; Brasil
dc.journal.title
Asian Journal of Organic Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ajoc.201900028
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1002/ajoc.201900028
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