The aza-Wittig reaction: an efficient tool for the construction of carbon-nitrogen double bonds

被引:386
作者
Palacios, Francisco [1 ]
Alonso, Concepcion [1 ]
Aparicio, Dornitila [1 ]
Rubiales, Gloria [1 ]
de los Santos, Jesus M. [1 ]
机构
[1] Univ Basque Country, Fac Farm, Dept Quim Organ 1, Vitoria 01080, Spain
关键词
D O I
10.1016/j.tet.2006.09.048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Recent advances in the aza-Wittig reaction of phosphazene derivatives with several carbonyl compounds are reviewed. Phosphazenes afford inter- and intramolecular aza-Wittig reactions with different compounds such as aldehydes, ketones, esters, thioesters, amides, anhydrides and sultimides. One of the most important applications of this reaction is the synthesis of a wide range of acyclic and heterocyclic compounds, ranging from simple monocyclic compounds to complex polycyclic and macrocyclic systems. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:523 / 575
页数:53
相关论文
共 243 条
[131]   ONE-POT SYNTHESIS OF A NEW CLASS OF FUSED 2,4-DIIMINO-1,3-DIAZETIDINES BY AN AZA-WITTIG [2+2] CYCLOADDITION OF CARBODIIMIDES PROCESS [J].
MOLINA, P ;
ARQUES, A ;
ALIAS, A ;
FOCESFOCES, MC ;
LLAMASSAIZ, AL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (05) :424-426
[132]  
MOLINA P, 1995, SYNLETT, P43
[133]   BIS(IMINOPHOSPHORANE)-MEDIATED 1,2,4-TRIAZOLO-ANNULATION ON IMIDAZOLE AND BENZIMIDAZOLE RINGS - PREPARATION OF IMIDAZO[1,2-B]-1,2,4-TRIAZOLES AND 1,2,4-TRIAZOLO[1,5-A]BENZIMIDAZOLES [J].
MOLINA, P ;
ALLER, E ;
LORENZO, A .
HETEROCYCLES, 1994, 37 (02) :997-1018
[134]   PREPARATION OF [5,6,6]-TRICYCLIC GUANIDINES FROM C,C-BIS(IMINOPHOSPHORANES) [J].
MOLINA, P ;
ALAJARIN, M ;
VIDAL, A .
TETRAHEDRON, 1995, 51 (18) :5351-5360
[135]  
Molina P, 1999, SYNTHESIS-STUTTGART, P326
[136]  
Molina P, 1996, SYNTHESIS-STUTTGART, P1459
[137]   Synthesis of marine alkaloids isonaamine A, dorimidazole A, and preclathridine A.: Iminophosphorane-mediated preparation of 2-amino-1,4-disubstituted imidazoles from α-azido esters [J].
Molina, P ;
Fresneda, PM ;
Sanz, MA .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2540-2544
[138]   PREPARATION, REACTIVITY AND SYNTHETIC APPLICATIONS OF BIS(IMINOPHOSPHORANES) - NEW ENTRIES TO FUSED 1,3,5-BENZOTRIAZEPINES, 1,3-BENZODIAZEPINES AND INDOLE-DERIVATIVES [J].
MOLINA, P ;
ARQUES, A ;
ALIAS, A ;
VINADER, MV ;
FOCESFOCES, MC ;
HERNANDEZCANO, F .
TETRAHEDRON, 1992, 48 (15) :3091-3110
[139]   SYNTHETIC APPLICATIONS OF C,C-BIS(IMINOPHOSPHORANES) - PREPARATION OF [5+5] RIGID BICYCLIC GUANIDINES AND 1,3,6-BENZOTHIADIAZEPINO[3,2-A] BENZIMIDAZOLE DERIVATIVES [J].
MOLINA, P ;
LIDON, MJ ;
TARRAGA, A .
TETRAHEDRON, 1994, 50 (33) :10029-10036
[140]   6-PI-ELECTROCYCLIZATION OF AZAHEXA-1,3,5-TRIENES - A NEW ENTRY TO A REGIOSPECIFIC SYNTHESIS OF 3-ARYL(HETEROARYL)PYRIDINES [J].
MOLINA, P ;
PASTOR, A ;
VILAPLANA, MJ .
TETRAHEDRON, 1993, 49 (35) :7769-7778