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4‐(Dimethylamino)Pyridinium Azide in Protic Ionic Liquid Media as a Stable Equivalent of Hydrazoic Acid Full article

Journal Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150
Output data Year: 2022, Volume: 364, Number: 14, Pages: 2403-2415 Pages count : 13 DOI: 10.1002/adsc.202200486
Authors Andreev Ivan A. 1 , Boichenko Maksim A. 2 , Ratmanova Nina K. 1 , Ivanova Olga A. 2 , Levina Irina I. 3 , Khrustalev Victor N. 4,5 , Sedov Igor A. 6 , Trushkov Igor V. 1,4
Affiliations
1 Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela st. 1, 117997 Moscow, Russian Federation
2 M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory 1–3, 119991 Moscow, Russian Federation
3 N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Kosygina st. 4, 119334 Moscow, Russian Federation
4 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, 119334 Moscow, Russian Federation
5 RUDN University, Faculty of Science, Miklukho-Maklaya st. 6, 117198 Moscow, Russian Federation
6 Chemical Institute, Kazan Federal University, Kremlevskaya st. 18, 420008 Kazan, Russian Federation

Abstract: 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.
Cite: Andreev I.A. , Boichenko M.A. , Ratmanova N.K. , Ivanova O.A. , Levina I.I. , Khrustalev V.N. , Sedov I.A. , Trushkov I.V.
4‐(Dimethylamino)Pyridinium Azide in Protic Ionic Liquid Media as a Stable Equivalent of Hydrazoic Acid
Advanced Synthesis & Catalysis. 2022. V.364. N14. P.2403-2415. DOI: 10.1002/adsc.202200486 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000818836200001
Scopus: 2-s2.0-85133062655
OpenAlex: W4282969302
Citing:
DB Citing
OpenAlex 20
Scopus 18
Web of science 16
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