Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(14): 2339-2342
DOI: 10.1055/s-2006-942432
DOI: 10.1055/s-2006-942432
PAPER
© Georg Thieme Verlag Stuttgart · New YorkTMSCl-Promoted Addition of Diethyl Phosphite to an Imine for the Synthesis of Bis[1-diethoxyphosphorylalkyl]amines
Further Information
Received
10 February 2006
Publication Date:
26 June 2006 (online)
Publication History
Publication Date:
26 June 2006 (online)

Abstract
A convenient preparative approach for the synthesis of bis[1-diethoxyphosphorylalkyl]amines has been developed. Treatment of aromatic aldehydes with ammonia and reaction with diethyl phosphite gives diethyl aryl[(arylmethylidene)amino]methylphosphonates, which can be easily reacted with diethyl phosphite in the presence of chlorotrimethylsilane to give bis[1-diethoxyphosphorylalkyl]amines. This method is easy, rapid, and good-yielding for the synthesis of bis[1-diethoxyphosphorylalkyl]amines from simple starting materials.
Key words
TMSCl - diethyl phosphite - imines - bis[1-diethoxyphosphorylalkyl]amines - addition reaction
- 1a
Engel R. Chem. Rev. 1977, 77: 349 - 1b
Hiratake J.Oda J. Biosci. Biotechnol. Biochem. 1997, 61: 211 - 1c
Schug KA.Lindner W. Chem. Rev. 2005, 105: 64 - 1d
Moonen K.Laureyn I.Stevens CV. Chem. Rev. 2004, 104: 6177 - 1e
Palacios F.Alonso C.de los Santos JM. Curr. Org. Chem. 2004, 8: 1481 - 2
Dingwall JG,Campell CD, andBaylis EK. inventors; UK Patent 1542938. ; Chem. Abstr. 1979, 88, 105559MissingFormLabel - 3
Kafarski P.Lejczak B.Tyka R.Koba L.Pliszczak E.Wieczorek P. J. Plant Growth Reg. 1995, 14: 199 - 4
Ishiguri Y,Yamada Y,Kato T,Sasaki M, andMukai K. inventors; EP 82301905. ; Chem. Abstr. 1983, 98, 102686MissingFormLabel - 5a
Gancarz R.Chakraborty S. Synthesis 1977, 625 - 5b
Giannousi PP.Bartlett PA. J. Med. Chem. 1987, 30: 1603 - 5c
Maier L.Lea PJ. Phosphorus Sulfur 1983, 17: 1 - 5d
Baylis EK.Campbell CD.Dingwall JG. J. Chem. Soc., Perkin Trans. 1 1984, 2445 - 5e
Hilderbrand RL. The Role of Phosphonates in Living Systems CRC Press; Boca Raton F1: 1982. - 6
Atherton FR.Hassal CH.Lambert RW. J. Med. Chem. 1987, 30: 1603 - 7
Allen MC.Fuhrer W.Tuck B.Wade R.Wood JM. J. Med. Chem. 1989, 32: 1652 - 8
Hassal CH. In Antibiotics Vol VI:Hahn FE. Springer Verlag; Berlin: 1983. p.1-11MissingFormLabel - 9
Kukhar VP.Hudson HR. Aminophosphonic and Aminophosphinic Acids Wiley; Chichester: 2000.MissingFormLabel - 10
Hyun-Joon H.Gong-Sil N. Synth. Commun. 1992, 22: 1143 - 11
Gancarz R.Wieczorek JS. Synthesis 1978, 625 - 12
Seyferth D.Marmor RS.Hilbert P. J. Org. Chem. 1971, 36: 1379 - 13
Worms KH.Schmidt-Dunker M. In Organic Phosphorus Compounds Vol. 7:Kosolapoff GM.Maier L. Wiley; New York: 1976. p.1MissingFormLabel - 14a
Berworth FC. inventors; US Patent 2599807. ; Chem. Abstr. 1953, 47, 4360b - 14b
Banks CV.Yerick RE. Anal. Chim. Acta 1959, 20: 301 - 15
Schwarzenbach G.Ackermann H.Ruckstuhl P. Helv. Chim. Acta 1944, 32: 1175 - 16a
Moedritzer K.Irani RR. J. Org. Chem. 1966, 31: 1603 - 16b
Dhawan B.Redmore D. J. Heterocycl. Chem. 1988, 25: 1273 - 16c
Iveson PB.Lowe MP.Lockhart JC. Polyhedron 1993, 12: 2313 - 17
Dimukhametov MN.Musin RZ.Buzykin BI.Latypov SK.Mironov VF. Mendeleev Commun. 2005, 40 - 18a
Sardarian AR.Kaboudin B. Tetrahedron Lett. 1997, 38: 2543 - 18b
Kaboudin B. Chem. Lett. 2001, 880 - 18c
Kaboudin B.Nazari R. Tetrahedron Lett. 2001, 42: 8211 - 18d
Kaboudin B.Nazari R. Synth. Commun. 2001, 31: 2241 - 18e
Kaboudin B.Balakrishna MS. Synth. Commun. 2002, 31: 2773 - 18f
Kaboudin B. Tetrahedron Lett. 2002, 43: 8713 - 18g
Kaboudin B. Tetrahedron Lett. 2003, 44: 1051 - 18h
Kaboudin B.Rahmani A. Synthesis 2003, 2705 - 18i
Kaboudin B.Saadati F. Synthesis 2004, 1249 - 19
Kaboudin B.Moradi K. Tetrahedron Lett. 2005, 46: 2989