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A new method for the synthesis of ?-aminoalkylidenebisphosphonates and their asymmetric phosphonyl-phosphinyl and phosphonyl-phosphinoyl analogues.

ABSTRACT: A convenient approach has been developed to ?-aminoalkylidenebisphosphonates and their asymmetric phosphonyl-phosphinyl and phosphonyl-phosphinoyl analogues by ?-phosphonylation, ?-phosphinylation or ?-phosphinoylation of 1-(N-acylamino)alkylphosphonates, that, in turn, are easily accessible from N-acyl-?-amino acids. Effective electrophilic activation of the ?-position of 1-(N-acetylamino)alkylphosphonates was achieved by electrochemical ?-methoxylation of these compounds in methanol, mediated with NaCl, followed by displacement of the methoxy group with triphenylphosphonium tetrafluoroborate to give hitherto unknown 1-(N-acetylamino)-1-triphenylphosphoniumalkylphosphonate tetrafluoroborates. The latter compounds react smoothly with trialkyl phosphites, dialkyl phosphonites or alkyl phosphinites in the presence of Hünig's base and methyltriphenylphosphonium iodide in a Michaelis-Arbuzov-like reaction to give the expected alkylidenebisphosphonates, 1-phosphinylalkylphosphonates or 1-phosphinoylalkylphosphonates, respectively, in good yields.

SUBMITTER: Kuznik A 

PROVIDER: S-EPMC4578414 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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A new method for the synthesis of α-aminoalkylidenebisphosphonates and their asymmetric phosphonyl-phosphinyl and phosphonyl-phosphinoyl analogues.

Kuźnik Anna A   Mazurkiewicz Roman R   Grymel Mirosława M   Zielińska Katarzyna K   Adamek Jakub J   Chmielewska Ewa E   Bochno Marta M   Kubica Sonia S  

Beilstein journal of organic chemistry 20150813

A convenient approach has been developed to α-aminoalkylidenebisphosphonates and their asymmetric phosphonyl-phosphinyl and phosphonyl-phosphinoyl analogues by α-phosphonylation, α-phosphinylation or α-phosphinoylation of 1-(N-acylamino)alkylphosphonates, that, in turn, are easily accessible from N-acyl-α-amino acids. Effective electrophilic activation of the α-position of 1-(N-acetylamino)alkylphosphonates was achieved by electrochemical α-methoxylation of these compounds in methanol, mediated  ...[more]

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