A Highly Efficient and Useful Synthetic Protocol for the Synthesis of Bis[aryl(diethoxyphosphoryl)methyl]amines from Aromatic Aldehydes Using Acetyl Chloride as an Efficient Catalyst

Abstract

A highly efficient and useful method for the synthesis of bis[aryl(diethoxyphosphoryl)methyl]amines has been developed. The treatment of aromatic aldehydes with ammonia followed by reaction with diethyl phosphite in the presence of acetyl chloride as catalyst gives bis[aryl(diethoxyphosphoryl)methyl]amines. This method is easy, rapid, and a high yielding method for the synthesis of bis[aryl(diethoxyphosphoryl)methyl]amines with good diastereo­selection from simple starting materials.

Key words

acetyl chloride - diethyl phosphite - aldehyde - bis[aryl(diethoxyphosphoryl)methyl]amine - addition reaction

References

• 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:  67 
• 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, Campbell CD, and Baylis EK. inventors; GB  1,542,938.  ; Chem. Abstr. 1979, 88, 105559j
• 3 Kafarski P. Lejczak B. Tyka R. Koba L. Pliszczak E. Wieczorek P. J. Plant Growth Regul.  1995,  14:  199 
• 4 Ishiguri Y, Yamada Y, Kato T, Sasaki M, and Mukai K. inventors; EP  0063464. 
• 5a Giannousis PP. Bartlett PA. J. Med. Chem.  1987,  30:  1603 
• 5b Maier L. Lea PJ. Phosphorus Sulfur Relat. Elem.  1983,  17:  1 
• 5c Baylis EK. Campbell CD. Dingwall JG. J. Chem. Soc., Perkin Trans. 1  1984,  2845 
• 5d Hilderbrand RL. In The Role of Phosphonates in Living Systems   CRC Press; Boca Raton: 1982. 
• 5e Kafarski P. Lejczak B. Phosphorus, Sulfur Silicon Relat. Elem.  1991,  63:  193 
• 5f Kukhar VP. Hudson HR. In Aminophos-phonic and Aminophosphinic Acids   John Wiley & Sons; Chichester: 2000. 
• 6 Atherton FR. Hassall CH. Lambert RW. J. Med. Chem.  1986,  29:  29 
• 7 Allen MC. Fuhrer W. Tuck B. Wade R. Wood JM. J. Med. Chem.  1989,  32:  1652 
• 8 Hassal CH. In Antibiotics   Vols. VI, 1-11:  Hahn FE. Springer Verlag; Berlin: 1983. 
• 9a Bhagat S. Chakraborti AK. J. Org. Chem.  2007,  72:  1263 
• 9b Kaboudin B. Phosphorus, Sulfur Silicon Relat. Elem.  2002,  177:  1749 
• 10 Gancarz R. Wieczorek JS. Synthesis  1978,  625 
• 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 Wiley & Sons; New York: 1976.  p.1 
• 13a Bersworth FC. inventors; US  2,599,807.  ; Chem. Abstr. 1953, 47, 4360b
• 13b Banks CV. Yerick RE. Anal. Chim. Acta  1959,  20:  301 
• 14 Schwarzenbach G. Ackermann H. Ruckstuhl P. Helv. Chim. Acta  1949,  32:  1175 
• 15a Moedritzer K. Irani RR. J. Org. Chem.  1966,  31:  1603 
• 15b Dhawan B. Redmore D. J. Heterocycl. Chem.  1988,  25:  1273 
• 15c Iveson PB. Lowe MP. Lockhart JC. Polyhedron  1993,  12:  2313 
• 16 Dimukhametov MN. Musin RZ. Buzykin BI. Latypov SK. Mironov VF. Mendeleev Commun.  2005,  40 
• 17a Sardarian AR. Kaboudin B. Tetrahedron Lett.  1997,  38:  2543 
• 17b Sardarian AR. Kaboudin B. Synth. Commun.  1997,  27:  543 
• 17c Kaboudin B. Chem. Lett.  2001,  880 
• 17d Kaboudin B. Nazari R. Tetrahedron Lett.  2001,  42:  8211 
• 17e Kaboudin B. Nazari R. Synth. Commun.  2001,  31:  2245 
• 17f Kaboudin B. Balakrishna MS. Synth. Commun.  2001,  31:  2773 
• 17g Kaboudin B. Tetrahedron Lett.  2002,  43:  8713 
• 17h Kaboudin B. Tetrahedron Lett.  2003,  44:  1051 
• 17i Kaboudin B. Rahmani A. Synthesis  2003,  2705 
• 17j Kaboudin B. Saadati F. Synthesis  2004,  1249 
• 17k Kaboudin B. Rahmani A. Org. Prep. Proced. Int.  2004,  36:  82 
• 17l Kaboudin B. Moradi K. Tetrahedron Lett.  2005,  46:  2989 
• 17m Kaboudin B. Haghighat H. Tetrahedron Lett.  2005,  46:  7955 
• 17n Kaboudin B. Haghighat H. Yokomatsu T. J. Org. Chem.  2006,  71:  6604 
• 17o Kaboudin B. Karimi M. Bioorg. Med. Chem. Lett.  2006,  16:  5324 
• 17p Kaboudin B. Farjadian F. Beilstein J. Org. Chem.  2006,  2:  4 ; http://bjoc.beilstein-journals.org/content/2/1/4
• 17q Kaboudin B. Moradi K. Tetrahedron Lett.  2005,  46:  2989 
• 17r Yamagishi T. Kusano T. Kaboudin B. Yokomatsu T. Sakuma C. Shibuya S. Tetrahedron  2003,  59:  767 
• 18a Tewari N. Nizar H. Mane A. George V. Prasad M. Synth. Commun.  2006,  36:  1911 
• 18b Ghosh R. Maiti S. Chakraborty A. Synlett  2005,  115 
• 18c Maeki AP. Paatero E. Salmi T. J. Chem. Technol. Biotechnol.  1994,  61:  1 
• 18d Patin H. Dabard R. Tetrahedron Lett.  1969,  10:  4971 
• 18e Sarvari MH. Synthesis  2005,  787 
• 19a Kaboudin B. Moradi K. Synthesis  2006,  2339 
• 19b Kaboudin B. Jafari E. Synthesis  2006,  3063