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Synthesis 2004(8): 1249-1252
DOI: 10.1055/s-2004-822350
DOI: 10.1055/s-2004-822350
PAPER
© Georg Thieme Verlag Stuttgart · New YorkStudies on the Synthesis of 1-Aminoalkylphosphonates from Aldehydes Using Silica-Supported Ammonium Hydrogen Carbonate
Further Information
Received
8 February 2004
Publication Date:
28 April 2004 (online)
Publication History
Publication Date:
28 April 2004 (online)

Abstract
Studies on the use of silica-supported ammonium hydrogen carbonate as an efficient reagent for the synthesis of 1-aminophosphonates under microwave irradiation in solvent-free conditions is reported. Investigations showed that this reaction proceeds by the formation of methanediamine as an intermediate. The reaction in the absence of diethyl phosphite gave cis-imidazolines as the major products.
Key words
1-aminophosphonates - silica - ammonium hydrogen carbonate - methanediamines - imidazolines
- 1a
Gancarz R.Chakraborty S. Synthesis 1977, 625 - 1b
Giannousi PP.Bartlett PA. J. Med. Chem. 1987, 30: 1603 - 1c
Maier L.Lea PJ. Phosphorus, Sulfur Relat. Elem. 1983, 17: 1 - 1d
Baylis EK.Campbell CD.Dingwall JG. J. Chem. Soc., Perkin Trans. 1 1984, 2445 - 1e
Hilderbrand RL. In The Role of Phosphonates in Living Systems CRC Press; Boca Raton F1: 1982. - 2
Kafarski P.Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63: 193 - 3
Hanessian S.Bennani YL. Synthesis 1995, 1272 - 4
Redmore D. In Topics in Phosphorus Chemistry Vol. 8:Griffith EJ.Grayson M. Wiley; New York: 1976. - 5
Allen MC.Fuhrer W.Tuck B.Wade R.Wood JM. J. Med. Chem. 1989, 32: 1652 - 6
Atherton FR.Hassal CH.Lambert RW. J. Med. Chem. 1987, 30: 1603 - 7
Hassal CH. In Antibiotics Vol VI:Hahn FE. Springer Verlag; Berlin: 1983. p.1-11 - 8a
Hirschmann R.Smith AB.Taylor CM.Benkovic PA.Taylor SD.Yager KM.Sprengler PA.Venkovic SJ. Science 1994, 265: 234 - 8b
Smith AB.Taylor CM.Venkovic SJ.Hirschmann R. Tetrahedron Lett. 1994, 37: 6854 - 9
Kukhar VP.Hudson HR. In Aminophosphonic and Aminophosphinic Acids John Wiley & Sons; Chichester: 2000. - 10a
Gancarz R.Wieczorek JS. Synthesis 1978, 625 - 10b
Yuan C.Lim C. Synthesis 1996, 507 - 10c
Yang R.Zhao R.Zhao L.Yun L.Wang H. Synthesis 2003, 887 - 11
Seyferth D.Marmor RS.Hilbert P. J. Org. Chem. 1971, 36: 1379 - 12
Worms KH.Schmidt-Dunker M. In Organic Phosphorus Compounds Vol. 7:Kosolapoff GM.Maier L. John Wiely & Sons; New York: 1976. p.1 - 13
Barycki J.Mastalers P. Tetrahedron Lett. 1970, 36: 3147 - 14a
Chakraborty S.Engel R. Synth. Commun. 1991, 21: 1039 - 14b
Manabe K.Kobayashi S. Chem. Commun. 2000, 669 - 14c
Maury C.Wang Q.Gharbaoui T.Chiadmi M.Tomas A.Royer J.Husson HP. Tetrahedron 1997, 53: 3627 - 14d
Vercruysse-Moreira K.Dejugnat C.Etemad-Moghadam G. Tetrahedron 2002, 58: 5651 - 15a
Oleksyszyn J.Subotkowska L.Mastalerz P. Synthesis 1979, 985 - 15b
Ryglowski A.Kafarski P. Tetrahedron 1996, 52: 10685 - 16a
Chalmers ME.Kosolapoff GM. J. Am. Chem. Soc. 1953, 75: 5278 - 16b
Takahashi H.Yoshioka M.Imai N.Onimura K.Kobayashi S. Synthesis 1994, 763 - 17a
Fadel A.Yefash R.Saluan J. Synthesis 1987, 37 - 17b
Rosini G.Galarini R.Marotta E.Righi R. J. Org. Chem. 1990, 55: 781 - 17c
Kodomari M.Sakamoto T.Yoshitomi S. J. Chem. Soc., Chem. Commun. 1990, 701 - 17d
Kropp PJ.Daus KA.Crawford SD.Tubergren MW.Kepler KD.Craig SL.Wilson VP. J. Am. Chem. Soc. 1990, 112: 7433 - 17e
Hondrogiannis G.Pagni RM.Kabalka GW.Anisoki P.Kurt R. Tetrahedron Lett. 1990, 31: 5433 - 17f
Pantney HK. Tetrahedron Lett. 1991, 32: 2259 - 17g
Pauter F.Daudon M. Tetrahedron Lett. 1991, 32: 1457 - 17h
Danks TN.Desai B. Green Chem. 2002, 4: 179 - 18a
Caddick S. Tetrahedron 1995, 55: 10403 - 18b
Zlotorzynsky A. Crit. Rev. Anal. Chem. 1995, 25: 43 - 18c
Varma RS. Green Chem. 1999, 43 - 18d
Lidstrom P.Tierney J.Wathey B.Westman J. Tetrahedron 2001, 57: 9225 - 18e
Perreux L.Loupy A. Tetrahedron 2001, 57: 9199 - 19
Kaboudin B. Chem. Lett. 2001, 880 - 20
Kaboudin B.Nazari R. Tetrahedron Lett. 2001, 42: 8211 - 21
Kaboudin B. Tetrahedron Lett. 2002, 43: 8713 - 22
Kaboudin B. Tetrahedron Lett. 2003, 44: 1051 - 23
Kaboudin B.Norouzi H. Tetrahedron Lett. 2004, 45: 1283 - 24
Kaboudin B.Rahmani A. Synthesis 2003, 2705 - 25a
Furth A. Monatsh. Chem. 1909, 17: 839 - 25b
Saigo K.Kubota N.Takebayashi S.Hasegawa M. Bull. Chem. Soc. Jpn. 1986, 59: 931 - 25c
Corey EJ.Kuhnle FNM. Tetrahedron Lett. 1997, 38: 8631 - 25d
Larter ML.Phillips M.Ortega F.Aguirre G.Somanathan R.Walsh PJ. Tetrahedron Lett. 1998, 39: 4785 - 25e
Mistrykov EA. Mendeleev Commun. 2001, 11: 29 - 25f
Lozinskaya NA.Tsybezova VV.Proskurnina MV.Zefirov NS. Russ. Chem. Bull. 2003, 52: 674 - 25g
Uchida H.Shimizu T.Reddy PY.Nakamura S.Toru T. Synthesis 2003, 1236 - 25h
Uchida H.Tanikoshi H.Nakamura S.Reddy PY.Toru T. Synthesis 2003, 1117 - 26
Sprung MM. Chem. Rev. 1940, 26: 297 - In fact, the reaction of N,N′-bis(phenylmethylidene)phenyl-methanediamine and diethyl phosphite has been reported in the literature:
- 27a
Kreutzkamp N.Cordes G. Liebigs Ann. Chem. 1959, 623: 103 - 27b
Rogozhin SV.Davankov VA.Belov YP. Izv. Akad. Nauk SSSR, Ser. Khim. 1973, 955 - 27c
Pudovik AN.Shagidullin RR.Khaiullin VK.Vandyukova II.Chernova AV.Gainullin RM.Pudovik MA. Izv. Akad. Nauk SSSR, Ser. Khim. 1996, 1303 - 27d
Soroka M.Kolodziejczyk K. Tetrahedron Lett. 2003, 44: 1863 - 28a
Corey EJ.Grogan MJ. Org. Lett. 1999, 1: 157 - 28b
Isobe T.Fukuda K.Araki Y.Ishikawa T. Chem. Commun. 2001, 243 - 28c
Anastassiadou M.Baziard-Mouysset G.Payard M. Synthesis 2000, 1814 - 28d
Corey EJ.Huang HC. Tetrahedron Lett. 1989, 30: 5235 - 28e
Corey EJ.Imwinkelried R.Pikul SB. J. Am. Chem. Soc. 1989, 111: 5493 - 28f
Corey EJ.Kim SS. J. Am. Chem. Soc. 1990, 112: 4976 - 28g
Corey EJ.Imai N.Pikul S.Xiang YB. Tetrahedron Lett. 1991, 32: 7517 - 28h
Evans DA.Nelson SG. J. Am. Chem. Soc. 1997, 119: 6452 - 29a
Hunter DH.Sim SK. J. Am. Chem. Soc. 1969, 91: 6202 - 29b
Hunter DH.Sim SK. Can. J. Chem. 1972, 50: 669 - 29c
Hunter DH.Sim SK. Can. J. Chem. 1972, 50: 678 - 30
Williams OF.Bailer JC. J. Am. Chem. Soc. 1959, 81: 4464