Subscribe to RSS
DOI: 10.1055/s-2007-983838
α-Iminotrifluoroethylphosphonates: The First Representatives of N-H Imidoyl Phosphonates
Publication History
Publication Date:
08 August 2007 (online)
![](https://www.thieme-connect.de/media/synthesis/200717/lookinside/thumbnails/10.1055-s-2007-983838-1.jpg)
Abstract
A convenient synthetic approach to previously unknown N-H imidoyl phosphonates, based on addition of dialkyl phosphites to trifluoroacetonitrile, has been developed. The synthetic potential of such imines, which exist as equilibrium mixtures of E/Z-isomers, was demonstrated by their easy reduction and functionalization with O- and P-centered nucleophiles, to afford derivatives of α-aminophosphonic acids containing a trifluoromethyl group. Furthermore, interaction with mercaptoacetic acid proceeds with intramolecular cyclization of the intermediate adduct to produce a novel 2-phosphorylated N-H thiazolidone. Interaction between the N-H imines and trichloroacetylisocyanate leads to novel, reactive, phosphorylated N-acylated imines.
Key words
imidoyl phosphonates - N-H imines - trifluoromethyl - aminophosphonates - E/Z-isomerism
-
1a
Rassukana YuV.Onys’ko PP.Davydova KO.Sinitsa AD. Eur. J. Org. Chem. 2004, 3643 -
1b
Rassukana YuV.Sinitsa AA.Onys’ko PP. Russ. Chem. Bull. 2005, 54: 2652 -
1c
Kolotilo NV.Sinitsa AA.Rassukana YuV.Onys’ko PP. Zh. Obshch. Khim. 2006, 76: 1260 ; Chem. Abstr. 2006, 146, 316980 -
2a
Pudovik AN.Zimin MG.Konovalova IV.Pozhidaev VM.Vinogradov LI. Zh. Obshch. Khim. 1975, 45: 30 ; Chem. Abstr. 1975, 82, 140262c -
2b
Zimin MG.Dvoinishnikova TA.Konovalova IV.Pudovik AN. Izv. Akad. Nauk SSSR, Ser. Khim. 1977, 499 ; Chem. Abstr. 1977, 88, 190978n -
3a
Gosselin Fr.O’Shea P.Roy S.Reamer R.Chen Ch.Volante R. Org. Lett. 2005, 7: 355 -
3b
Chen G.-M.Brown HC. J. Am. Chem. Soc. 2000, 122: 4217 ; and references therein - 4
Onys’ko PP.Kim TV.Kiseleva EI.Pustovit YuM.Sinitsa AD. Zh. Obshch. Khim. 2005, 75: 1263 ; Chem. Abstr. 2005, 145, 43868 -
5a In
Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity
Kukhar VP.Hudson HR. Chichester, Wiley & Sons; N.Y.: 2000. -
5b
Cherkasov RA.Galkin VI. Usp. Khim. 1998, 67: 940 -
6a
Onys’ko PP.Kim TV.Kiseleva EI.Sinitsa AD. Zh. Obshch. Khim. 2004, 74: 1981 ; Chem. Abstr. 2004, 143, 267027 -
6b
Flynn GA.Beight DW.Boehme EHW. Tetrahedron Lett. 1985, 26: 285 -
6c
Titanyuk ID.Vorob’eva DV.Osipov SN.Beletskaya IP. Synlett 2006, 1355 -
7a
Russel G. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 144: 793 -
7b
Ebetino FH. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 144: 9 -
7c
Widler L.Jaeggi KA.Green JR. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 144: 5 -
7d
Mönkkönen J.Makkonen N.Rogers MJ.Frith JC.Auriola S. Phosphorus, Sulfur Silicon Relat. Elem. 1999, 144: 321 - 8
Onys’ko PP.Rassukana YuV.Sinitsa AD. Zh. Obshch. Khim. 2002, 72: 1802 ; Chem. Abstr. 2002, 139, 101198 -
9a
Sinitsa OA.Kolotilo NV.Onys’ko PP. Ukr. Chem. J. 1998, 64: 5 ; Chem. Abstr. 1998, 131, 228737 -
9b
Onys’ko PP. Zh. Obshch. Khim. 1999, 69: 158 ; Chem. Abstr. 1999, 131, 257626 -
9c
Kolotilo NV.Sinitsa AA.Onys’ko PP. Russ. Chem. Bull. 1998, 47: 2044 - 10
Onys’ko PP.Kim TV.Kiseleva EI.Pirozhenko VV.Sinitsa AD. Ukr. Khim. Zh. 2002, 68: 68 ; Chem. Abstr. 2002, 139, 53080