AI Article Synopsis
- The research focuses on transforming α-EWG-substituted γ-azidobutyronitriles through unique aza-Wittig reactions that lead to the creation of pyrrole-derived iminophosphazenes.
- The presence and type of α-EWGs influence chemoselectivity, functioning either as activators or competitors for the nitrile group in these reactions.
- The resulting iminophosphazenes are further utilized as N,N-binucleophiles to synthesize more complex structures like pyrrole-fused systems, pyrrolo[1,2-a]imidazoles, and pyrrolo[1,2-a][1,3]diazepines.
Article Abstract
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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| http://dx.doi.org/10.1021/acs.orglett.8b04135 | DOI Listing |
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