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Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles
A one-pot iodine-catalyzed multicomponent reaction has been developed for the selective preparation of 5-amino-4-(arylselanyl)-1H-pyrazoles from a diverse array of benzoylacetonitriles, arylhydrazines and diaryl diselenides. The reactions were conducted in MeCN as solvent at reflux temperature under...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6244180/ https://www.ncbi.nlm.nih.gov/pubmed/30498528 http://dx.doi.org/10.3762/bjoc.14.256 |
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author | Pires, Camila S de Oliveira, Daniela H Pontel, Maria R B Kazmierczak, Jean C Cargnelutti, Roberta Alves, Diego Jacob, Raquel G Schumacher, Ricardo F |
author_facet | Pires, Camila S de Oliveira, Daniela H Pontel, Maria R B Kazmierczak, Jean C Cargnelutti, Roberta Alves, Diego Jacob, Raquel G Schumacher, Ricardo F |
author_sort | Pires, Camila S |
collection | PubMed |
description | A one-pot iodine-catalyzed multicomponent reaction has been developed for the selective preparation of 5-amino-4-(arylselanyl)-1H-pyrazoles from a diverse array of benzoylacetonitriles, arylhydrazines and diaryl diselenides. The reactions were conducted in MeCN as solvent at reflux temperature under air. The methodology presents a large functional group tolerance to electron-deficient, electron-rich, and bulky substituents and gave the expected products in good to excellent yields. The synthesized 1,3-diphenyl-4-(phenylselanyl)-1H-pyrazol-5-amine was submitted to an oxidative dehydrogenative coupling to produce a diazo compound confirmed by X-ray analysis. |
format | Online Article Text |
id | pubmed-6244180 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-62441802018-11-29 Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles Pires, Camila S de Oliveira, Daniela H Pontel, Maria R B Kazmierczak, Jean C Cargnelutti, Roberta Alves, Diego Jacob, Raquel G Schumacher, Ricardo F Beilstein J Org Chem Full Research Paper A one-pot iodine-catalyzed multicomponent reaction has been developed for the selective preparation of 5-amino-4-(arylselanyl)-1H-pyrazoles from a diverse array of benzoylacetonitriles, arylhydrazines and diaryl diselenides. The reactions were conducted in MeCN as solvent at reflux temperature under air. The methodology presents a large functional group tolerance to electron-deficient, electron-rich, and bulky substituents and gave the expected products in good to excellent yields. The synthesized 1,3-diphenyl-4-(phenylselanyl)-1H-pyrazol-5-amine was submitted to an oxidative dehydrogenative coupling to produce a diazo compound confirmed by X-ray analysis. Beilstein-Institut 2018-11-06 /pmc/articles/PMC6244180/ /pubmed/30498528 http://dx.doi.org/10.3762/bjoc.14.256 Text en Copyright © 2018, Pires et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Pires, Camila S de Oliveira, Daniela H Pontel, Maria R B Kazmierczak, Jean C Cargnelutti, Roberta Alves, Diego Jacob, Raquel G Schumacher, Ricardo F Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles |
title | Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles |
title_full | Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles |
title_fullStr | Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles |
title_full_unstemmed | Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles |
title_short | Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles |
title_sort | molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1h-pyrazoles |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6244180/ https://www.ncbi.nlm.nih.gov/pubmed/30498528 http://dx.doi.org/10.3762/bjoc.14.256 |
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