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1-吲唑及其4-、5-、6-和7-硝基衍生物在盐酸水溶液中与甲醛加成机理的研究。

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

作者信息

Alkorta Ibon, Claramunt Rosa M, Elguero José, Gutiérrez-Puebla Enrique, Monge M Ángeles, Reviriego Felipe, Roussel Christian

机构信息

Instituto de Química Médica, CSIC, Juan de la Cierva, 3, E-28006 Madrid, Spain.

Departamento de Química Orgánica y Bio-Orgánica, Facultad de Ciencias, UNED, Senda del Rey 9, E-28040 Madrid, Spain.

出版信息

J Org Chem. 2022 May 6;87(9):5866-5881. doi: 10.1021/acs.joc.2c00154. Epub 2022 Apr 11.

DOI:10.1021/acs.joc.2c00154
PMID:35405072
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9087356/
Abstract

The reaction of -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 -CHOH 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-indazol-1-yl)methanol derivatives are reported.

摘要

通过溶液和固态核磁共振（NMR）以及晶体学对吲唑与甲醛在盐酸水溶液中的反应进行了实验研究。确定了-CHOH衍生物的形成机制。首次通过多核NMR对2-取代衍生物进行了表征。理论上，在Becke三参数（交换）Lee-Yang-Parr B3LYP/6-311++G(d,p)水平上使用规范不变原子轨道（GIAO）进行的计算为实验观察提供了可靠的基础。报道了四种（1-吲唑-1-基）甲醇衍生物的首个X射线结构。

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