Open AccessStudy of the Addition Mechanism of 1H-Indazole and Its 4-, 5-, 6-, and 7-Nitro Derivatives to Formaldehyde in Aqueous Hydrochloric Acid Solutions
Author(s) -
Ibón Alkorta,
Rosa M. Claramunt,
José Elguero,
Enrique GutiérrezPuebla,
Ángeles Monge,
Felipe Reviriego,
Christian Roussel
Publication year - 2022
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.2c00154
Subject(s) - formaldehyde , hydrochloric acid , chemistry , aqueous solution , methanol , indazole , nitro , reaction mechanism , inorganic chemistry , medicinal chemistry , computational chemistry , organic chemistry , catalysis , alkyl
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 (1 H -indazol-1-yl)methanol derivatives are reported.