Trifluoroethanol as a metal-free, homogeneous and recyclable medium for the efficient one-pot synthesis of α-amino nitriles and α-amino phosphonates

被引：69

作者：

Heydari, Akbar ^{[1
]}

Khaksar, Samad ^{[1
]}

Tajbakhsh, Mahmood ^{[2
]}

机构：

[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran

[2] Mazandaran Univ, Dept Chem, Babol Sar 47415, Iran

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 01期

关键词：

Fluorous solvents; Trimethylsilyl cyanide; Trifluoroethanol; alpha-Amino phosphonates; alpha-Amino nitriles; Hydrogen bonding; ORGANIC PHOSPHORUS-COMPOUNDS; FACILE SYNTHESIS; ENANTIOSELECTIVE ADDITION; 3-COMPONENT CONDENSATION; LANTHANIDE TRIFLATE; SOLVENT-FREE; ACID; ALDEHYDES; CATALYST; AMINOPHOSPHONATES;

D O I：

10.1016/j.tetlet.2008.10.106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trifluoroethanol is found to be an efficient and recyclable medium in promoting one-pot, three-component coupling reactions of aldehydes or ketones, amines and trimethylsilyl cyanide or trimethyl phosphite to afford the corresponding (alpha-amino nitriles or alpha-amino phosphonates in high yields. This protocol does not require the use of an acid or base catalyst. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：77 / 80

页数：4

共 57 条

[1] RENIN INHIBITORS - SYNTHESIS OF TRANSITION-STATE ANALOG INHIBITORS CONTAINING PHOSPHORUS-ACID DERIVATIVES AT THE SCISSILE BOND
ALLEN, MC
FUHRER, W
TUCK, B
WADE, R
WOOD, JM
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) : 1652 - 1661
[2] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID
ATHERTON, FR
HASSALL, CH
LAMBERT, RW
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (01) : 29 - 40
[3] Fluorinated alcohols:: A new medium for selective and clean reaction
Bégué, JP
Bonnet-Delpon, D
Crousse, B
[J]. SYNLETT, 2004, (01) : 18 - 29
[4] An extremely efficient three-component reaction of aldehydes/ketones, amines, and phosphites (Kabachnik-Fields reaction) for the synthesis of α-aminophosphonates catalyzed by magnesium perchlorate
Bhagat, Srikant
Chakraborti, Asit K.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) : 1263 - 1270
[5] Total synthesis of the alkaloid (-)-codonopsinine from L-xylose
Chandrasekhar, S
Jagadeshwar, V
Prakash, SJ
[J]. TETRAHEDRON LETTERS, 2005, 46 (17) : 3127 - 3129
[6] Three component coupling catalyzed by TaCl5-SiO2:: synthesis of α-amino phosphonates
Chandrasekhar, S
Prakash, SJ
Jagadeshwar, V
Narsihmulu, C
[J]. TETRAHEDRON LETTERS, 2001, 42 (32) : 5561 - 5563
[7] RuCl3 catalyzed one-pot synthesis of α-aminonitriles
De, SK
[J]. SYNTHETIC COMMUNICATIONS, 2005, 35 (05) : 653 - 656
[8] Vanadyl triflate as an efficient and recyclable catalyst for trimethylsilyl cyanide addition to carbonyl compounds
De, SK
Gibbs, RA
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 232 (1-2) : 123 - 125
[9] Nickel(II) chloride catalyzed one-pot synthesis of α-aminonitriles
De, SK
[J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 225 (02) : 169 - 171
[10] Bismuth trichloride catalyzed synthesis of α-aminonitriles
De, SK
Gibbs, RA
[J]. TETRAHEDRON LETTERS, 2004, 45 (40) : 7407 - +

← 1 2 3 4 5 6 →