4-(Dimethylamino)Pyridinium Azide in Protic Ionic Liquid Media as a Stable Equivalent of Hydrazoic Acid,Advanced Synthesis & Catalysis

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4-(Dimethylamino)Pyridinium Azide in Protic Ionic Liquid Media as a Stable Equivalent of Hydrazoic Acid
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-06-15 , DOI: 10.1002/adsc.202200486
Ivan Andreev ₁ , Maksim Boichenko ₂ , Nina Ratmanova ₁ , Olga Ivanova ₃ , Irina Levina ₄ , Victor Khrustalev ₅ , Igor Sedov ₆ , Igor Trushkov ₇

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We report a procedure for the multigram synthesis of 4-(dimethylamino)pyridinium azide, a stable, non-explosive, low-hygroscopic source of azide ion soluble in both protic and aprotic organic solvents. In protic ionic liquid media this reagent was shown to serve as a safer equivalent of toxic and unstable hydrazoic acid. The synthetic utility of this system was demonstrated using donor-acceptor cyclopropane ring opening as a model process. General procedures furnishing a variety of dialkyl (2-azido-2-arylethyl)malonates or 4-azido-4-arylbutyrates, depending on the protic ionic liquid applied, were elaborated. The conversion times for studied donor-acceptor cyclopropanes were established providing the relative reactivity sequence. The application of 4-(dimethylamino)pyridinium azide for a conventional nucleophilic substitution, oxirane ring opening, (3+2)-cycloaddition to (thio)cyano group as well as their combinations realized as telescopic synthesis was also demonstrated.

中文翻译：

质子离子液体介质中的 4-(二甲氨基)叠氮化吡啶鎓作为叠氮酸的稳定等效物

我们报告了一种多克合成 4-(二甲氨基) 叠氮化吡啶鎓的过程，这是一种稳定、非爆炸性、低吸湿性的叠氮化物离子源，可溶于质子和非质子有机溶剂。在质子离子液体介质中，该试剂被证明可作为有毒且不稳定的叠氮酸的更安全等效物。使用供体-受体环丙烷开环作为模型过程证明了该系统的合成效用。详细说明了根据所应用的质子离子液体提供各种 (2-叠氮基-2-芳乙基) 丙二酸二烷基酯或 4-叠氮基-4-芳基丁酸二烷基酯的一般程序。建立所研究的供体-受体环丙烷的转化时间，提供相对反应性序列。4-(二甲氨基)吡啶叠氮在常规亲核取代、环氧乙烷开环中的应用，

更新日期：2022-06-15

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