A mild and highly efficient protocol for the one-pot synthesis of primary α-amino phosphonates under solvent-free conditions

被引：90

作者：

Azizi, N ^{[1
]}

Rajabi, F ^{[1
]}

Saidi, MR ^{[1
]}

机构：

[1] Sharif Univ Technol, Dept Chem, Tehran 11365, Iran

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 50期

关键词：

D O I：

10.1016/j.tetlet.2004.10.092

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under solvent-free reaction conditions and in the presence of solid LiClO4 a novel and mild protocol for the one-pot, three-component synthesis of primary alpha-amino phosphonates from an aldehyde, hexamethyldisilazane and a trialkyl phosphite is described giving high yields and having short reaction times. The same products are obtained in very low yields, when the three-component reaction is carried out under microwave irradiation and in the absence of solid LiClO4. Examples of some prepared 1-aryl-N,N'-bis(arylidene)inethanediamines are also described. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：9233 / 9236

页数：4

相关论文

共 38 条

[1] RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND [J].

ALLEN, MC ;

FUHRER, W ;

TUCK, B ;

WADE, R ;

WOOD, JM .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) :1652-1661

[2] Lithium perchlorate mediated three-component preparation of α-aminonitriles under solvent-free conditions [J].

Azizi, N ;

Saidi, MR .

SYNTHETIC COMMUNICATIONS, 2004, 34 (07) :1207-1214

[3] Novel and efficient method for the silylation of hydroxyl groups with hexamethyldisilazane (HMDS) under solvent-free and neutral conditions [J].

Azizi, N ;

Saidi, MR .

ORGANOMETALLICS, 2004, 23 (06) :1457-1458

[4] LiClO4 accelerated Michael addition of amines to α,β-unsaturated olefins under solvent-free conditions [J].

Azizi, N ;

Saidi, MR .

TETRAHEDRON, 2004, 60 (02) :383-387

[5] An improved synthesis of cyanohydrins in the presence of solid LiClO4 under solvent-free conditions [J].

Azizi, N ;

Saidi, MR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 688 (1-2) :283-285

[6] A novel procedure for conversion of epoxides to α-hydroxyphosphonates with a trialkylphosphite mediated by LiClO4 [J].

Azizi, N ;

Said, MR .

TETRAHEDRON LETTERS, 2003, 44 (43) :7933-7935

[7] Synthesis of tertiary α-amino phosphonate by one-pot three-component coupling mediated by LPDE [J].

Azizi, N ;

Saidi, MR .

TETRAHEDRON, 2003, 59 (28) :5329-5332

[8] PHOSPHINIC ACID DIPEPTIDE ANALOGS - POTENT, SLOW-BINDING INHIBITORS OF ASPARTIC PEPTIDASES [J].

BARTLETT, PA ;

KEZER, WB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (15) :4282-4283

[9] A NOVEL ROUTE TO ALPHA-AMINOALKYLPHOSPHONIC ACIDS AND DIALKYL ALPHA-AMINOALKYLPHOSPHONATE HYDROCHLORIDES [J].

BERLIN, KD ;

ROY, NK ;

CLAUNCH, RT ;

BUDE, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (16) :4494-&

[10] THE SYNTHESIS OF AMINO-SUBSTITUTED PHOSPHONIC ACIDS .3. [J].

CHALMERS, ME ;

KOSOLAPOFF, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (21) :5278-5280

← 1 2 3 4 →