Aziridination of α,β-unsaturated phosphonic esters

被引:23
作者
Fazio, A [1 ]
Loreto, MA [1 ]
Tardella, PA [1 ]
机构
[1] Univ La Sapienza, Ctr CNR Studio Chim Sostanze Organ Nat, Dipartimento Chim, I-00185 Rome, Italy
关键词
aziridines; phosphonic acids and derivatives;
D O I
10.1016/S0040-4039(01)00063-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthetic precursors of amino phosphonic acids are aziridinyl phosphonates. These compounds can be prepared through a reaction of phosphonates 2a-e with NsONHCO(2)Et and inorganic bases involving addition of an (ethoxycarbonyl)amino group onto the double bond, via a new and easy procedure. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2185 / 2187
页数:3
相关论文
共 14 条
[1]   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
[2]   3-Acetoxyaminoquinazolinones (QNHOAc) as aziridinating agents: ring-opening of N-(Q)-substituted aziridines [J].
Atkinson, RS .
TETRAHEDRON, 1999, 55 (06) :1519-1558
[3]   Aziridination of alpha,beta-unsaturated esters by (ethoxycarbonyl)nitrene [J].
Carducci, M ;
Fioravanti, S ;
Loreto, MA ;
Pellacani, L ;
Tardella, PA .
TETRAHEDRON LETTERS, 1996, 37 (21) :3777-3778
[4]   Synthesis of natural products containing a C-P bond [J].
Fields, SC .
TETRAHEDRON, 1999, 55 (42) :12237-12272
[5]   A NOVEL ROUTE TO N-SUBSTITUTED ALLYLAMINES BY THE REACTION OF ALLYLSILANES WITH (ETHOXYCARBONYL)NITRENE [J].
FIORAVANTI, S ;
LORETO, MA ;
PELLACANI, L ;
RAIMONDI, S ;
TARDELLA, PA .
TETRAHEDRON LETTERS, 1993, 34 (25) :4101-4104
[6]   Solvent-free aziridination of α-nitroalkenes [J].
Fioravanti, S ;
Pellacani, L ;
Stabile, S ;
Tardella, PA ;
Ballini, R .
TETRAHEDRON, 1998, 54 (22) :6169-6176
[7]  
HRISCHMANN R, 1994, SCIENCE, V265, P234
[8]  
Kim DY, 1997, TETRAHEDRON, V53, P13603
[9]   CARBETHOXYNITRENE BY ALPHA-ELIMINATION . REACTIONS WITH HYDROCARBONS [J].
LWOWSKI, W ;
MARICICH, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (16) :3630-&
[10]   Recent synthetic applications of chiral aziridines [J].
McCoull, W ;
Davis, FA .
SYNTHESIS-STUTTGART, 2000, (10) :1347-1365