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Updated: May 9, 2025

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
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亚司匹龙酸衍生物的三组合合成

Ali Oudi1, Abbas Ali Esmaeili2, Azizollah Habibi3

  • 1Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad, Iran.

Scientific reports
|April 30, 2025
PubMed
概括

一种新的无催化剂的多元组分反应有效地使用异酸/乙基构建块合成复杂的螺旋异环. 这种绿色化学方法为创建新型分子架构提供了一种实用且具有成本效益的方法.

关键词:
1-Oxo-2-oxa-3-azaspiro[4.4]nona-3,6,8-triene的使用情况4-利丁-异醇-5(4H) -一个-一个.基于多元组件反应的反应.异酸盐是什么? 异酸盐是什么?螺旋螺旋的异环循环.三个组成部分的反应反应.

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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