Study of the Addition Mechanism of 1 H -Indazole and Its 4-, 5-, 6-, and 7-Nitro Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions - Aix-Marseille Université Access content directly
Journal Articles Journal of Organic Chemistry Year : 2022

Study of the Addition Mechanism of 1 H -Indazole and Its 4-, 5-, 6-, and 7-Nitro Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions

Abstract

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.
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hal-03959333 , version 1 (07-02-2023)

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Ibon Alkorta, Rosa Claramunt, José Elguero, Enrique Gutiérrez-Puebla, M. Ángeles Monge, et al.. Study of the Addition Mechanism of 1 H -Indazole and Its 4-, 5-, 6-, and 7-Nitro Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions. Journal of Organic Chemistry, 2022, 87 (9), pp.5866-5881. ⟨10.1021/acs.joc.2c00154⟩. ⟨hal-03959333⟩
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