1-(N-Acylamino)-1-triphenylphosphoniumalkylphosphonates: General synthesis and prospects for further synthetic applications |
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Authors: | Anna Kuźnik Roman Mazurkiewicz Magdalena Zięba Karol Erfurt |
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Institution: | 1. Department of Organic and Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland;2. Biotechnology Center of Silesian University of Technology, B. Krzywoustego 8, 44-100 Gliwice, Poland;3. Department of Organic Chemical Technology and Petrochemistry, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland |
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Abstract: | A general approach for the synthesis of 1-(N-acylamino)-1-triphenylphosphoniumalkylphosphonates from readily accessible alkyl imidate hydrochlorides has been developed. The three-step synthesis involves acylation of the imidate hydrochloride with an acyl chloride, the Michaelis–Becker-like addition of diethyl phosphite to the N–acylimidate and subsequent nucleophilic substitution of the ethoxy group of the 1–ethoxyphosphonate derivative with triphenylphosphonium tetrafluoroborate. 1–(N–Acylamino)-1-triphenylphosphoniumalkylphosphonates were demonstrated to be promising intermediates for further synthetic transformations toward α-functionalized derivatives of α–aminophosphonic acids and α,β-dehydro-α-aminophosphonates. |
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Keywords: | α β–Dehydro-α-aminophosphonates Bisphosphonates |
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