The Reactions of Diethyl 2,3-Dihydro-4h-1,3-Benzoxazin-4-One-2-Phosphonate With Nucleophiles

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

“…by α-bromination of 1-aminophosphonates with N -bromosuccinimide [28,38–41] or by alkoxylation or aryloxylation of this position [20,29–30]. …”

“…2), reported by Kostka and Kotyński in 1990–1993 was the synthesis of diethyl 1-( N -salicyloylamino)-1-diphenylphosphinoylmethylphosphonate (Fig. 2, 4 : R = Ph, R 1 = H, R 2 = o -HOC 6 H 4 CO, R 3 = Et) by condensation of diethyl 2,3-dihydro-4 H -1,3-benzoxazin-4-one-2-phosphonate with diphenylphosphine oxide [29] or diphenyltrimethylsilyloxyphosphine [Ph 2 POSiMe 3 ] [30]. In 2004–2007, Onys’ko et al reported the synthesis of diethyl or diphenyl 1-( N -phenylsulfonylamino)-1-diphenylphosphinoylmethylphosphonate derivatives (Fig.…”

A method for the synthesis of unsymmetric bisphosphoric analogs of α-amino acids

“…Such an example is the synthesis of diethyl 1-( N -salicyloylamino)-1-diphenylphosphinoylmethylphosphonate described by Kostka and Kotyński, one of the first methods for the preparation of this type of bisphosphoric derivative that was carried out with a yield of 15% or 47% depending on the type of nucleophile used (Scheme 1, route A). 17,18 In addition to that, there are only two known routes for the preparation of 1-amino-1-phosphinoylalkylphosphonates. One of them consists of the reaction of diphenylphosphine oxide with iminophosphonate derivatives activated by the presence of trifluoromethyl 19 or a p -fluorophenyl group 20 at the α-carbon atom provided the desired product in yields of 60–91% (Scheme 1, route B).…”