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<i>aza</i>-Wittig Reaction with Nitriles: How Carbonyl Function Switches from Reacting to Activating

Hamidulla B. TukhtaevDepartment of Chemistry, Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, RussiaKonstantin 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

Organic Lettersjournal2019en

ABI

Annotatsiya

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.

Mavzular

Phosphorus compounds and reactions Synthesis and Reactivity of Heterocycles Synthesis and Reactivity of Sulfur-Containing Compounds

Identifikatorlar

DOI: 10.1021/acs.orglett.8b04135

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