A Novel Method for the Synthesis of Bis(1-diethoxyphosphorylalkyl)amines from Diimines

Babak Kaboudin; Ehsan Jafari

doi:10.1055/s-2006-942541

PAPER

A Novel Method for the Synthesis of Bis(1-diethoxyphosphorylalkyl)amines from Diimines

Babak Kaboudin*, Ehsan Jafari
Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Gava Zang, Zanjan 45195-1159, Iran
Fax: +98(241)4249023; e-Mail: kaboudin@iasbs.ac.ir;

Abstract

Alle Artikel dieser Rubrik

Abstract

A novel and convenient method for the synthesis of bis(1-diethoxyphosphorylalkyl) amines has been developed. As described below, treatment of aromatic diimines with diethyl phosphite in the presence of chlorotrimethylsilane gave 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 - diethylphosphite - diimines - bis(1-diethoxyphosphorylalkyl)amines - addition reaction

Volltext

Referenzen

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: 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, and Baylis EK. inventors; UK Pat. Appl., 1542938. ; 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; Eur. Pat. Appl., EP 82301905. ; Chem. Abstr., 1983, 98, 102686u

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. In 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.1-11

9 Kukhar VP. Hudson HR. In Aminophosphonic and Aminophosphinic Acids John Wiley & Sons; Chichester: 2000.

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. John Wiley & Sons; New York: 1976. p.P.1

14a Berworth FC. inventors; U.S. 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

18j Kaboudin B. Rahmani A. Org. Prep. Proced. Int. 2004, 36: 82

18k Kaboudin B. Farjadian F. Beilstein J. Org. Chem. 2006, 2: 4

19 Kaboudin B. Moradi K. Tetrahedron Lett. 2005, 46: 2989

20 Kaboudin B. Moradi K. Synthesis 2006, 2339

21a Furth A. Monatsh. Chem. 1909, 17: 839

21b Saigo K. Kubota N. Takebayashi S. Hasegawa M. Bull. Chem. Soc. Jpn. 1986, 59: 931

21c Corey EJ. Kuhnle FNM. Tetrahedron Lett. 1997, 38: 8631

21d Larter ML. Phillips M. Ortega F. Aguirre G. Somanathan R. Walsh PJ. Tetrahedron Lett. 1998, 39: 4785

21e Mistrykov EA. Mendeleev Commun. 2001, 11: 29

21f Lozinskaya NA. Tsybezova VV. Proskurnina MV. Zefirov NS. Russ. Chem. Bull. 2003, 52: 674

21g Nishiyama K. Saito M. Oba M. Bull. Chem. Soc. Jpn. 1988, 61: 609

21h Grigors SV. Zh. Obshch. Khim. 2001, 71: 163 ; Russ. J. Gen. Chem. (Engl. Transl.) 2001, 71, 149

21i Uchida H. Shimizu T. Reddy PY. Nakamura S. Toru T. Synthesis 2003, 1236

21j Uchida H. Tanikoshi H. Nakamura S. Reddy PY. Toru T. Synthesis 2003, 1117

21k Kaboudin B. Saadati F. Heterocycles 2005, 65: 353

22a Corey EJ. Grogan MJ. Org. Lett. 1999, 1: 157

22b Isobe T. Fukuda K. Araki Y. Ishikawa T. Chem. Commun. 2001, 243

22c Anastassiadou M. Baziard-Mouysset G. Payard M. Synthesis 2000, 1814

22d Corey EJ. Huang HC. Tetrahedron Lett. 1989, 30: 5235

22e Corey EJ. Imwinkelried R. Pikul SB. J. Am. Chem. Soc. 1989, 111: 5493

22f Corey EJ. Kim SS. J. Am. Chem. Soc. 1990, 112: 4976

22g Corey EJ. Imai N. Pikul S. Xiang YB. Tetrahedron Lett. 1991, 32: 7517

22h Evans DA. Nelson SG. J. Am. Chem. Soc. 1997, 119: 6452