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Study of the Addition Mechanism of 1H-Indazole and Its 4-, 5-, 6-, and 7-Nitro Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions
[Image: see text] The reaction of NH-indazoles with formaldehyde in aqueous hydrochloric acid has been experimentally studied by solution and solid-state nuclear magnetic resonance (NMR) and crystallography. The mechanism of the formation of N(1)-CH(2)OH derivatives was determined. For the first tim...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9087356/ https://www.ncbi.nlm.nih.gov/pubmed/35405072 http://dx.doi.org/10.1021/acs.joc.2c00154 |
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author | Alkorta, Ibon Claramunt, Rosa M. Elguero, José Gutiérrez-Puebla, Enrique Monge, M. Ángeles Reviriego, Felipe Roussel, Christian |
author_facet | Alkorta, Ibon Claramunt, Rosa M. Elguero, José Gutiérrez-Puebla, Enrique Monge, M. Ángeles Reviriego, Felipe Roussel, Christian |
author_sort | Alkorta, Ibon |
collection | PubMed |
description | [Image: see text] The reaction of NH-indazoles with formaldehyde in aqueous hydrochloric acid has been experimentally studied by solution and solid-state nuclear magnetic resonance (NMR) and crystallography. The mechanism of the formation of N(1)-CH(2)OH derivatives was determined. For the first time, 2-substituted derivatives have been characterized by multinuclear NMR. Theoretically, calculations with gauge-invariant atomic orbitals (GIAOs) at the Becke three-parameter (exchange) Lee–Yang–Parr B3LYP/6-311++G(d,p) level have provided a sound basis for the experimental observations. The first X-ray structures of four (1H-indazol-1-yl)methanol derivatives are reported. |
format | Online Article Text |
id | pubmed-9087356 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-90873562022-05-11 Study of the Addition Mechanism of 1H-Indazole and Its 4-, 5-, 6-, and 7-Nitro Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions Alkorta, Ibon Claramunt, Rosa M. Elguero, José Gutiérrez-Puebla, Enrique Monge, M. Ángeles Reviriego, Felipe Roussel, Christian J Org Chem [Image: see text] The reaction of NH-indazoles with formaldehyde in aqueous hydrochloric acid has been experimentally studied by solution and solid-state nuclear magnetic resonance (NMR) and crystallography. The mechanism of the formation of N(1)-CH(2)OH derivatives was determined. For the first time, 2-substituted derivatives have been characterized by multinuclear NMR. Theoretically, calculations with gauge-invariant atomic orbitals (GIAOs) at the Becke three-parameter (exchange) Lee–Yang–Parr B3LYP/6-311++G(d,p) level have provided a sound basis for the experimental observations. The first X-ray structures of four (1H-indazol-1-yl)methanol derivatives are reported. American Chemical Society 2022-04-11 2022-05-06 /pmc/articles/PMC9087356/ /pubmed/35405072 http://dx.doi.org/10.1021/acs.joc.2c00154 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Alkorta, Ibon Claramunt, Rosa M. Elguero, José Gutiérrez-Puebla, Enrique Monge, M. Ángeles Reviriego, Felipe Roussel, Christian Study of the Addition Mechanism of 1H-Indazole and Its 4-, 5-, 6-, and 7-Nitro Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions |
title | Study of the Addition
Mechanism of 1H-Indazole and Its 4-,
5-, 6-, and 7-Nitro
Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions |
title_full | Study of the Addition
Mechanism of 1H-Indazole and Its 4-,
5-, 6-, and 7-Nitro
Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions |
title_fullStr | Study of the Addition
Mechanism of 1H-Indazole and Its 4-,
5-, 6-, and 7-Nitro
Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions |
title_full_unstemmed | Study of the Addition
Mechanism of 1H-Indazole and Its 4-,
5-, 6-, and 7-Nitro
Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions |
title_short | Study of the Addition
Mechanism of 1H-Indazole and Its 4-,
5-, 6-, and 7-Nitro
Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions |
title_sort | study of the addition
mechanism of 1h-indazole and its 4-,
5-, 6-, and 7-nitro
derivatives to formaldehyde in aqueous hydrochloric acid solutions |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9087356/ https://www.ncbi.nlm.nih.gov/pubmed/35405072 http://dx.doi.org/10.1021/acs.joc.2c00154 |
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