Microwave-Enhanced Synthesis of Phosphonoacetamides

REFERENCES

• (a) Fleisch , H. Bisphosphonates in osteoporosis: An introduction. Osteoporosis Internat. 1993, Suppl. 3, S3–S5; (b) Russell , R. G. G. ; Rogers , M. J. Introduction to bisphosphonates and the clinical pharmacology of alendronate. Brit. J. Rheumatol. 1997, Suppl. 1, 10–14; (c) Mathew , M. ; Fowler , B. O. ; Golomb , G. ; Alferiev , I. F. ; Eidelman , N. Synthesis, characterization, and crystal structure of dicalcium glutarylbis(phosphonate) dihydrate: A covalently pillared layer structure with the potential for epitaxial growth of hydroxyapatite. Inorg. Chem. 1998, 37, 6485–6494; (d) Räsänen , J. P. ; Pohlaja , E. ; Nikander , H. ; Pakkanen , T. A. Ab initio studies on organophosphorus compounds, 6: Interactions of dimethylphosphinic and dimethylphosphinothioic acid monoanions and methylenebisphosphonic acid dianion with calcium. J. Phys. Chem. A 1997, 101, 5196–5204; (e) Ochocki , J. ; Erxleben , A. ; Lippert , B. Synthesis and spectroscopy of phosphonate derivatives of uracil and thymine: X-ray crystal structure of diethyl 6-uracylmethylphosphonate. J. Heterocycl. Chem. 1997, 34, 1179–1184.
   Google Scholar
• (a) Kannan , S. ; Venugopal , V. Synthesis and characterization of mononuclear and dinuclear adducts of carbamylmethylenephosphonate with uranyl bis (β-diketonates) . Polyhedron 1995 , 14 , 2349 – 2354 ; (b) Belciug , M. P. ; Modro , A. M. ; Modro , T. A. ; Wessels , P. L. Metal ion complexation by the phosphoryl and the carbonyl groups probed by 17O NMR spectroscopy . J. Phys. Org. Chem. 1995 , 8 , 605 – 609 ; (c) McCabe , J. ; Bowen , S. M. ; Paine , R. T. Synthesis of dialkyl [1,2-bis(diethylcarbamoyl)ethyl]-phosphonates . Synthesis 1986 , 319 – 320 .
   Web of Science ®Google Scholar
• Gall , I. L. ; Laurent , P. ; Soulier , E. ; Salaün , J. Y. ; Abbayes , J. Complexation on rhodium of bidentate and potentially hemilabile phophorous ligands . J. Organomet. Chem. 1998 , 567 , 13 – 20 .
   Web of Science ®Google Scholar
• Gagnard , V. ; Leydet , A. ; Le Mellay , V. ; Aubenque , M. ; Morère , A. ; Montero , J.-L. Synthesis and biological evaluation of S-acyl-3-thiopropyl prodrugs of N-phosphonoacetyl L-aspartate (PALA) . Eur. J. Med. Chem. 2003 , 38 , 883 – 891 .
   PubMed Web of Science ®Google Scholar
• Eldo , J. ; Heng , S. ; Kantrowitz , E. R. Design, synthesis, and bioactivity of novel inhibitors of E. coli aspartate transcarbamoylase . Bioorg. Med. Chem. Lett. 2007 , 17 , 2086 – 2090 .
   PubMed Web of Science ®Google Scholar
• Ando , K. Preparations of (Z)-α,β-unsaturated amides by using Horner–Wadsworth–Emmons reagents, (diphenylphosphono)acetamides . Synlett 2001 , 1272 – 1274 .
   Web of Science ®Google Scholar
• (a) Antonioletti , R. ; Bonadies , F. ; Cardilli , A. ; Lattanzi , A. ; Orelli , L. R. ; Scettri , A. A new procedure for Horner–Wadsworth–Emmons olefination of carbonyl compounds . Tetrahedron Lett. 1994 , 35 , 3383 – 3386 ; (b) Lattanzi , A. ; Orelli , L. R. ; Barone , P. ; Mazza , A. ; Iannece , P. ; Scettri , A. Convenient procedure of Horner–Wadsworth–Emmons olefination for the synthesis of simple and functionalized α,β-unsaturated nitriles . Tetrahedron Lett. 2003 , 44 , 1333 – 1337 .
   Web of Science ®Google Scholar
• (a) Arbuzov , A. E. On the structure of phosphonic acid and its derivates: Isometization and transition of bonds from trivalent to pentavalent phosphorus . J. Russ. Phys. Chem. Soc. 1906 , 38 , 687 ; (b) Michaelis , A. E. ; Kaehne , R. Ueber das Verhalten der Jodalkyle gegen die sogen: Phosphorigsäureester oder O-Phosphine . Chem. Ber. 1898 , 31 , 1048 .
   Google Scholar
• (a) Balsigier , R. W. ; Jones , D. G. ; Montgomery , J. A. Synthesis of potential anticancer agents, XVIII: Analogs of carbamoyl phosphate . J. Org. Chem. 1959 , 24 , 434 – 436 ; (b) Kem , K. M. ; Nguyen , N. V. ; Cross , D. J. Phase-transfer-catalyzed Michaelis–Becker reaction . J. Org. Chem. 1981 , 46 , 5188 – 5192 .
   Web of Science ®Google Scholar
• Hatakeshama , S. ; Satoh , K. ; Sakurai , K. ; Takano , S. Efficient ester exchange reaction of phosphonacetates . Tetrahedron Lett. 1987 , 28 , 2713 – 2716 .
   Web of Science ®Google Scholar
• Among others, (a) Grison , C. ; Coutrot , P. ; Comoy , C. ; Balas , L. ; Joliez , S. ; Lavecchia , G. ; Oliger , P. ; Penverne , B. ; Serre , V. ; Hervé , G. Design, synthesis, and activity of bisubstrate, transition-state analogues, and competitive inhibitors of aspartate transcarbamylase . Eur. J. Med. Chem. 2004 , 39 , 333 – 344 ; (b) Saltmarsh , J. R. ; Boyd , A. E. ; Rodríguez , O. P. ; Radié , Z. ; Taylor , P. ; Thompson , C. M. Synthesis of fluorescent probes directed to the active site gorge of acetylcholinesterase . Bioorg. Med. Chem. Lett. 2000 , 10 , 1523 – 1526 .
   PubMed Web of Science ®Google Scholar
• Tay , M. K. ; About-Jaudet , E. ; Colignon , N. ; Savignac , P. Phosphonates α-lithies, agents de transfert fonctionnel: Preparation de phosphonates α-amides et d'amides α,β-insatures, α-substitues. Tetrahedron Lett. 1989, 45, 4415–4430.
   Web of Science ®Google Scholar
• Walker , B. J. Organophosphorus Chemistry Specialist Periodical Reports ; Chemical Society : London , 1970 – 1979 ; vol. 1–10, chapter 5 .
   Google Scholar
• Bhattacharya , A. K. ; Thyagarajan , G. The Michaelis–Arbuzov rearrangement . Chem. Rev. 1981 , 81 , 415 – 430 .
   Web of Science ®Google Scholar
• Marques Rodrigues , J. ; Neves da Costa , J. B. Synthesis and characterization of new symmetrical bisphosphonates . Phosphorus, Sulfur Silicon Relat. Elem. 2002 , 177 , 137 – 149 .
   Web of Science ®Google Scholar
• Kiddle , J. ; Gurley , A. F. Microwave irradiation in organophosphorus chemistry 1: The Michaelis–Arbuzov reaction . Phosphorus, Sulfur Silicon Relat. Elem. 2000 , 160 , 195 – 205 .
   Web of Science ®Google Scholar
• Engel , R. Synthesis of Carbon–Phosphorus Bonds ; CRC Press : Boca Raton , FL , 1988 .
   Google Scholar
• Among others, (a) Loupy , A. Microwaves in Organic Synthesis ; Wiley-VCH : Weinheim , 2002 ; (b) Kappe , C. O. ; Dallinger , D. The impact of microwave synthesis on drug discovery. Nat. Rev. Drug. Discover. 2006, 5, 51–63 ; (c) Kappe , C. O. Controlled microwave heating in modern organic synthesis. Angew. Chem. Int. Ed. 2004, 43, 6250–6284 ; (d) Shipe , W. D. ; Wolkenberg , S. E. ; Lindsley , C. W. Accelerated lead development by microwave-enhanced medicinal chemistry. Drug Discovery Today: Technol. 2005, 2, 155–161 ; (e) Lindström , P. ; Tierney , J. ; Wathey , B. ; Westman , J. Microwave-assisted organic synthesis—A review. Tetrahedron 2001, 57, 9225–9283 ; (f) Caddick , S. Microwave-assisted organic reactions. Tetrahedron 2005, 51, 10403–10432 ; (g) Kappe , C. O. ; Dallinger , D. Controlled microwave heating in modern organic synthesis: Highlights from the 2004–2008 literature. Mol. Diversity 2009, 13, 71–193 .
   Google Scholar
• Perreux , L. ; Loupy , A. A tentative rationalization of microwave effects in organic synthesis according to the reaction medium and mechanistic considerations . Tetrahedron 2001 , 57 , 9199 – 9223 .
   Web of Science ®Google Scholar
• (a) Garner , A. Y. ; Chapin , E. C. ; Scanlon , P. M. Mechanism of the Michaelis–Arbuzov reaction: Olefin formation . J. Org. Chem. 1959 , 24 , 532 – 536 ; (b) Hudson , H. R. Quasi-phosphonium intermediates and compounds . Top. Phosphophorus Chem. 1983 , 11 , 339 .
   Web of Science ®Google Scholar
• Kiddle , J. Microwave irradiation in organophosphorus chemistry, III: Moderate scale synthesis of reagents for olefin formation . Synth. Commun. 2001 , 31 , 171 – 176 .
   Web of Science ®Google Scholar
• Kingston , H. M. ; Haswell , S. J. Microwave-Enhanced Chemistry ; American Chemical Society : Washington , DC , 1997 .
   Google Scholar
• García , M. B. ; Torres , R. A. ; Orelli , L. R. Microwave-enhanced synthesis of cyclic amidines . Tetrahedron Lett. 2006 , 47 , 4857 – 4859 .
   Web of Science ®Google Scholar
• Link , N. P. ; Díaz , J. E. ; Orelli , L. R. An efficient synthesis of N-arylputrescines and cadaverines . Synlett 2009 , 5 , 751 – 754 .
   Google Scholar
• Worms , K. H. ; Schmidt-Dunker , M. Organic Phosphorus Compounds ; John Wiley and Sons : New York , 1976 ; vol. 7 , p. 24 .
   Google Scholar
• Orelli , L. R. ; Gruber , N. NMR spectroscopic study of some novel N,N-disubstituted phosphonoacetamides . J. Mol. Struct. 2009 , 921 , 215 – 218 .
   Web of Science ®Google Scholar
• Speziale , A. J. ; Freeman , R. C. Reactions of phosphorus compounds, I: Diethyl carbamoylmethylphosphonates . J. Org. Chem. 1958 , 23 , 1883 – 1885 .
   Web of Science ®Google Scholar
• Namboodiri , V. V. ; Varma , R. S. An improved preparation of 1,3-dialkylimidazolium tetrafluoroborate ionic liquids using microwaves . Tetrahedron Lett. 2002 , 43 , 5381 .
   Web of Science ®Google Scholar