Amberlite-IR 120 catalyzed three-component synthesis of α-amino phosphonates in one-pot

被引:107
作者
Bhattacharya, Asish K. [1 ]
Rana, Kalpeshkumar C.
机构
[1] Natl Chem Lab, Combi Chem Bio Resource Ctr, Pune 411008, Maharashtra, India
关键词
alpha-amino phosphonates; aldehydes; amines; alkyl phosphite; ion-exchange resin; multi-component reaction;
D O I
10.1016/j.tetlet.2008.02.102
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, efficient, and environmentally benign method for a three-component reaction of an amine, an aldehyde or a ketone, and diethyl phosphite catalyzed by Amberlite-IR 120 resin has been developed to afford alpha-amino phosphonates in high yields and short reaction times under solvent-free reaction conditions. The major advantages of the present method are good yields, inexpensive, ecofriendly and reusable catalyst, mild and solvent-free reaction conditions and tolerance towards various functionalities present in the substrates. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2598 / 2601
页数:4
相关论文
共 25 条
[1]   Resin-supported acid- and base-catalyzed one-pot sequential reaction including an enantioselective step [J].
Akagawa, Kengo ;
Sakamoto, Seiji ;
Kudo, Kazuaki .
TETRAHEDRON LETTERS, 2007, 48 (06) :985-987
[2]   PHOSPHONOPEPTIDES, A NEW CLASS OF SYNTHETIC ANTIBACTERIAL AGENTS [J].
ALLEN, JG ;
ATHERTON, FR ;
HALL, MJ ;
HASSALL, CH ;
HOLMES, SW ;
LAMBERT, RW ;
NISBET, LJ ;
RINGROSE, PS .
NATURE, 1978, 272 (5648) :56-58
[3]   PHOSPHONOPEPTIDES AS ANTIBACTERIAL AGENTS - ALAPHOSPHIN AND RELATED PHOSPHONOPEPTIDES [J].
ALLEN, JG ;
ATHERTON, FR ;
HALL, MJ ;
HASSALL, CH ;
HOLMES, SW ;
LAMBERT, RW ;
NISBET, LJ ;
RINGROSE, PS .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 15 (05) :684-695
[4]   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
[5]   PHOSPHONOPEPTIDES AS ANTIBACTERIAL AGENTS - MECHANISM OF ACTION OF ALAPHOSPHIN [J].
ATHERTON, FR ;
HALL, MJ ;
HASSALL, CH ;
LAMBERT, RW ;
LLOYD, WJ ;
RINGROSE, PS .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 15 (05) :696-705
[6]   SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF ANTIBACTERIAL PHOSPHONOPEPTIDES INCORPORATING (1-AMINOETHYL)PHOSPHONIC ACID AND (AMINOMETHYL)PHOSPHONIC ACID [J].
ATHERTON, FR ;
HASSALL, CH ;
LAMBERT, RW .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (01) :29-40
[7]   PHOSPHONOPEPTIDES AS ANTIBACTERIAL AGENTS - RATIONALE, CHEMISTRY, AND STRUCTURE-ACTIVITY-RELATIONSHIPS [J].
ATHERTON, FR ;
HALL, MJ ;
HASSALL, CH ;
LAMBERT, RW ;
RINGROSE, PS .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1979, 15 (05) :677-683
[8]   An efficient one-pot synthesis of α-amino phosphonates catalyzed by bismuth nitrate pentahydrate [J].
Bhattacharya, Asish K. ;
Kaur, Tanpreet .
SYNLETT, 2007, (05) :745-748
[9]   MICROWAVE-ASSISTED ORGANIC-REACTIONS [J].
CADDICK, S .
TETRAHEDRON, 1995, 51 (38) :10403-10432
[10]   A PRACTICAL SYNTHESIS OF ALPHA-AMINOPHOSPHONIC ACIDS [J].
GENET, JP ;
UZIEL, J ;
PORT, M ;
TOUZIN, AM ;
ROLAND, S ;
THORIMBERT, S ;
TANIER, S .
TETRAHEDRON LETTERS, 1992, 33 (01) :77-80