EFFICIENT METHOD FOR THE SYNTHESIS OF α-AMIDOPHOSPHONATES VIA THE MICHAELIS-ARBUZOV REACTION

被引：10

作者：

Lakoud, Samia Guezane ^{[1
]}

Berredjem, Malika ^{[1
]}

Aouf, Nour-Eddine ^{[1
]}

机构：

[1] Badji Mokhtar Univ, Lab Appl Organ Chem, El Hadjar, Annaba, Algeria

来源：

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2012年 / 187卷 / 06期

关键词：

Phosphonate; beta-ketophosphonate; alpha-amidophosphonate; arbuzov reaction; becker reaction; PHOSPHONATES; ANALOGS; AGENTS;

D O I：

10.1080/10426507.2011.645173

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new series of modified alpha-amidophosphonates (or beta-ketophosphonate) was synthesized by an efficient method, starting from aminoesters and chloroacetyl chloride. We have established that chloroacetyl chloride is a suitable reagent allowing the introduction a halogen moiety for the Arbuzov reaction. The a-amidophosphonates were prepared in two steps (acetylation, phosphorylation).

引用

页码：762 / 768

页数：7

共 19 条

[1] THE MICHAELIS-ARBUZOV REARRANGEMENT [J].

BHATTACHARYA, AK ;

THYAGARAJAN, G .

CHEMICAL REVIEWS, 1981, 81 (04) :415-430

[2] Diastereoselective synthesis of α-substituted β-amidophosphonates [J].

Castelot-Deliencourt, G ;

Pannecoucke, X ;

Quirion, JC .

TETRAHEDRON LETTERS, 2001, 42 (06) :1025-1028

[3] Efficient synthesis of protected L-phosphonophenylalanine (Ppa) derivatives suitable for solid phase peptide synthesis [J].

Chauhan, Satendra S. ;

Varshney, Arti ;

Verma, Bhavana ;

Pennington, Michael W. .

TETRAHEDRON LETTERS, 2007, 48 (23) :4051-4054

[4] Selective one-pot synthesis of substituted pyrrole-3-phosphonates from α-cyanomethyl-β-ketoesters [J].

Demir, Ayhan S. ;

Tural, Servet .

TETRAHEDRON, 2007, 63 (19) :4156-4161

[5] PHOSPHONATES AS ANALOGS OF NATURAL PHOSPHATES [J].

ENGEL, R .

CHEMICAL REVIEWS, 1977, 77 (03) :349-367

[6]

Eto M., 1992, HDB ORGANOPHOSPHORUS, P807

[7] Synthesis of natural products containing a C-P bond [J].

Fields, SC .

TETRAHEDRON, 1999, 55 (42) :12237-12272

[8] ISOLATION OF 2-AMINOETHANE PHOSPHONIC ACID FROM RUMEN PROTOZOA [J].

HORIGUCHI, M ;

KANDATSU, M .

NATURE, 1959, 184 (4690) :901-902

[9]

Kafarski P., 2000, AMINOPHOSPHONIC AMIN, P407

[10]

KALIR A, 1996, CHEM ORGANOPHOSPHORU, V4, P767

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