<i>aza</i>-Wittig Reaction with Nitriles: How Carbonyl Function Switches from Reacting to Activating
Hamidulla B. TukhtaevInstitute of Bioorganic Chemistry, Uzbek Academy of Sciences, Mirzo Ulugbek str. 83, Tashkent 100125, UzbekistanKonstantin L. IvanovDepartment of Chemistry, Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, RussiaStanislav I. BezzubovKurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskiy pr. 31, Moscow 119991, RussiaDmitry CheshkovState Scientific Research Institute of Chemistry and Technology of Organoelement Compounds, Sh. Entuziastov 38, Moscow 105118, RussiaMikhail Ya. MelnikovDepartment of Chemistry, Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, RussiaЕкатерина М. БудынинаDepartment of Chemistry, Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, Russia
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Transformations of α-EWG-substituted (electron-withdrawing group, EWG) γ-azidobutyronitriles proceeding via unusual aza-Wittig reactions between the phosphazene and nitrile functions and affording pyrrole-derived iminophosphazenes were developed. α-EWGs were found to control chemoselectivity and, depending on their nature, act as CN group activators (e.g., ester, amide, or nitrile) or competitors (e.g., ketone) in aza-Wittig reactions. To demonstrate the synthetic utility of the obtained iminophosphazenes as N, N-binucleophiles, their transformations into pyrrole-fused systems, pyrrolo[1,2- a]imidazoles and pyrrolo[1,2- a][1,3]diazepines, were carried out.
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