An Efficient Synthesis of 2-CF(3)-3-Benzylindoles

The reaction of α-CF(3)-β-(2-nitroaryl) enamines with benzaldehydes afforded effectively α,β-diaryl-CF(3)-enones having nitro group. Subsequent reduction of nitro group by NH(4)HCO(2)-Pd/C system initiated intramolecular cyclization to give 2-CF(3)-3-benzylindoles. Target products can be prepared in...

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Autores principales: Muzalevskiy, Vasiliy M., Sizova, Zoia A., Nenajdenko, Valentine G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8401147/
https://www.ncbi.nlm.nih.gov/pubmed/34443672
http://dx.doi.org/10.3390/molecules26165084
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author Muzalevskiy, Vasiliy M.
Sizova, Zoia A.
Nenajdenko, Valentine G.
author_facet Muzalevskiy, Vasiliy M.
Sizova, Zoia A.
Nenajdenko, Valentine G.
author_sort Muzalevskiy, Vasiliy M.
collection PubMed
description The reaction of α-CF(3)-β-(2-nitroaryl) enamines with benzaldehydes afforded effectively α,β-diaryl-CF(3)-enones having nitro group. Subsequent reduction of nitro group by NH(4)HCO(2)-Pd/C system initiated intramolecular cyclization to give 2-CF(3)-3-benzylindoles. Target products can be prepared in up to quantitative yields. Broad synthetic scope of the reaction was shown. Probable mechanism of indole formation is proposed.
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spelling pubmed-84011472021-08-29 An Efficient Synthesis of 2-CF(3)-3-Benzylindoles Muzalevskiy, Vasiliy M. Sizova, Zoia A. Nenajdenko, Valentine G. Molecules Article The reaction of α-CF(3)-β-(2-nitroaryl) enamines with benzaldehydes afforded effectively α,β-diaryl-CF(3)-enones having nitro group. Subsequent reduction of nitro group by NH(4)HCO(2)-Pd/C system initiated intramolecular cyclization to give 2-CF(3)-3-benzylindoles. Target products can be prepared in up to quantitative yields. Broad synthetic scope of the reaction was shown. Probable mechanism of indole formation is proposed. MDPI 2021-08-22 /pmc/articles/PMC8401147/ /pubmed/34443672 http://dx.doi.org/10.3390/molecules26165084 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Muzalevskiy, Vasiliy M.
Sizova, Zoia A.
Nenajdenko, Valentine G.
An Efficient Synthesis of 2-CF(3)-3-Benzylindoles
title An Efficient Synthesis of 2-CF(3)-3-Benzylindoles
title_full An Efficient Synthesis of 2-CF(3)-3-Benzylindoles
title_fullStr An Efficient Synthesis of 2-CF(3)-3-Benzylindoles
title_full_unstemmed An Efficient Synthesis of 2-CF(3)-3-Benzylindoles
title_short An Efficient Synthesis of 2-CF(3)-3-Benzylindoles
title_sort efficient synthesis of 2-cf(3)-3-benzylindoles
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8401147/
https://www.ncbi.nlm.nih.gov/pubmed/34443672
http://dx.doi.org/10.3390/molecules26165084
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