TMSCl-Promoted Addition of Diethyl Phosphite to an Imine for the Synthesis of Bis[1-diethoxyphosphorylalkyl]amines

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.

TMSCl - diethyl phosphite - imines - bis[1-diethoxyphosphorylalkyl]amines - addition reaction

References

<A NAME="RZ03306SS-1A">1a</A> Engel R. Chem. Rev.  1977,  77:  349 

<A NAME="RZ03306SS-1B">1b</A> Hiratake J. Oda J. Biosci. Biotechnol. Biochem.  1997,  61:  211 

<A NAME="RZ03306SS-1C">1c</A> Schug KA. Lindner W. Chem. Rev.  2005,  105:  64 

<A NAME="RZ03306SS-1D">1d</A> Moonen K. Laureyn I. Stevens CV. Chem. Rev.  2004,  104:  6177 

<A NAME="RZ03306SS-1E">1e</A> Palacios F. Alonso C. de los Santos JM. Curr. Org. Chem.  2004,  8:  1481 

<A NAME="RZ03306SS-2">2</A> Dingwall JG, Campell CD, and Baylis EK. inventors; UK Patent  1542938.  ; Chem. Abstr. 1979, 88, 105559

<A NAME="RZ03306SS-3">3</A> Kafarski P. Lejczak B. Tyka R. Koba L. Pliszczak E. Wieczorek P. J. Plant Growth Reg.  1995,  14:  199 

<A NAME="RZ03306SS-4">4</A> Ishiguri Y, Yamada Y, Kato T, Sasaki M, and Mukai K. inventors; EP  82301905.  ; Chem. Abstr. 1983, 98, 102686

<A NAME="RZ03306SS-5A">5a</A> Gancarz R. Chakraborty S. Synthesis  1977,  625 

<A NAME="RZ03306SS-5B">5b</A> Giannousi PP. Bartlett PA. J. Med. Chem.  1987,  30:  1603 

<A NAME="RZ03306SS-5C">5c</A> Maier L. Lea PJ. Phosphorus Sulfur  1983,  17:  1 

<A NAME="RZ03306SS-5D">5d</A> Baylis EK. Campbell CD. Dingwall JG. J. Chem. Soc., Perkin Trans. 1  1984,  2445 

<A NAME="RZ03306SS-5E">5e</A> Hilderbrand RL. The Role of Phosphonates in Living Systems   CRC Press; Boca Raton F1: 1982. 

<A NAME="RZ03306SS-6">6</A> Atherton FR. Hassal CH. Lambert RW. J. Med. Chem.  1987,  30:  1603 

<A NAME="RZ03306SS-7">7</A> Allen MC. Fuhrer W. Tuck B. Wade R. Wood JM. J. Med. Chem.  1989,  32:  1652 

<A NAME="RZ03306SS-8">8</A> Hassal CH. In Antibiotics   Vol VI:  Hahn FE. Springer Verlag; Berlin: 1983.  p.1-11  

<A NAME="RZ03306SS-9">9</A> Kukhar VP. Hudson HR. Aminophosphonic and Aminophosphinic Acids   Wiley; Chichester: 2000. 

<A NAME="RZ03306SS-10">10</A> Hyun-Joon H. Gong-Sil N. Synth. Commun.  1992,  22:  1143 

<A NAME="RZ03306SS-11">11</A> Gancarz R. Wieczorek JS. Synthesis  1978,  625 

<A NAME="RZ03306SS-12">12</A> Seyferth D. Marmor RS. Hilbert P. J. Org. Chem.  1971,  36:  1379 

<A NAME="RZ03306SS-13">13</A> Worms KH. Schmidt-Dunker M. In Organic Phosphorus Compounds   Vol. 7:  Kosolapoff GM. Maier L. Wiley; New York: 1976.  p.1 

<A NAME="RZ03306SS-14A">14a</A> Berworth FC. inventors; US Patent  2599807.  ; Chem. Abstr. 1953, 47, 4360b

<A NAME="RZ03306SS-14B">14b</A> Banks CV. Yerick RE. Anal. Chim. Acta  1959,  20:  301 

<A NAME="RZ03306SS-15">15</A> Schwarzenbach G. Ackermann H. Ruckstuhl P. Helv. Chim. Acta  1944,  32:  1175 

<A NAME="RZ03306SS-16A">16a</A> Moedritzer K. Irani RR. J. Org. Chem.  1966,  31:  1603 

<A NAME="RZ03306SS-16B">16b</A> Dhawan B. Redmore D. J. Heterocycl. Chem.  1988,  25:  1273 

<A NAME="RZ03306SS-16C">16c</A> Iveson PB. Lowe MP. Lockhart JC. Polyhedron  1993,  12:  2313 

<A NAME="RZ03306SS-17">17</A> Dimukhametov MN. Musin RZ. Buzykin BI. Latypov SK. Mironov VF. Mendeleev Commun.  2005,  40 

<A NAME="RZ03306SS-18A">18a</A> Sardarian AR. Kaboudin B. Tetrahedron Lett.  1997,  38:  2543 

<A NAME="RZ03306SS-18B">18b</A> Kaboudin B. Chem. Lett.  2001,  880 

<A NAME="RZ03306SS-18C">18c</A> Kaboudin B. Nazari R. Tetrahedron Lett.  2001,  42:  8211 

<A NAME="RZ03306SS-18D">18d</A> Kaboudin B. Nazari R. Synth. Commun.  2001,  31:  2241 

<A NAME="RZ03306SS-18E">18e</A> Kaboudin B. Balakrishna MS. Synth. Commun.  2002,  31:  2773 

<A NAME="RZ03306SS-18F">18f</A> Kaboudin B. Tetrahedron Lett.  2002,  43:  8713 

<A NAME="RZ03306SS-18G">18g</A> Kaboudin B. Tetrahedron Lett.  2003,  44:  1051 

<A NAME="RZ03306SS-18H">18h</A> Kaboudin B. Rahmani A. Synthesis  2003,  2705 

<A NAME="RZ03306SS-18I">18i</A> Kaboudin B. Saadati F. Synthesis  2004,  1249 

<A NAME="RZ03306SS-19">19</A> Kaboudin B. Moradi K. Tetrahedron Lett.  2005,  46:  2989