α-Halogenohydrazides:: useful starting material for the synthesis of hydrazinoazapeptides and azauracils

被引:3
作者
Barré, C [1 ]
Carret, S [1 ]
Guerro, M [1 ]
Le Grel, P [1 ]
Baudy-Floc'h, M [1 ]
机构
[1] Univ Rennes 1, CNRS, UMR 6510, Grp Synthese & Electrosynth Organ, F-35042 Rennes, France
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1999年 / 77卷 / 02期
关键词
hydrazinohydrazides; hydrazones; hydrazinoazapeptides; azaaminouracils; pseudopeptides;
D O I
10.1139/cjc-77-2-263
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient method for the synthesis of pseudodipeptides, which combines an aza glycine residue with various hydrazinoacid moieties by simple substitution of the halogen of alpha-halohydrazides, is described, Some of these hydrazinoazapeptides lead to hydrazones by oxidation or to azaaminouracils by cyclization.
引用
收藏
页码:263 / 270
页数:8
相关论文
共 20 条
[1]  
AMOUR A, 1994, INT J PEPT PROT RES, V43, P297
[2]   DESIGN AND SYNTHESIS OF A NEW SERIES OF PEPTIDE ANALOGS - THE HYDRAZINOPEPTIDES [J].
BARRE, C ;
LEGREL, P ;
ROBERT, A ;
BAUDYFLOCH, M .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (05) :607-607
[3]  
BAYER, 1976, Patent No. 3966715
[4]   PRACTICAL SYNTHESIS OF CYCLIC-PEPTIDES, WITH AN EXAMPLE OF DEPENDENCE OF CYCLIZATION YIELD UPON LINEAR SEQUENCE [J].
BRADY, SF ;
VARGA, SL ;
FREIDINGER, RM ;
SCHWENK, DA ;
MENDLOWSKI, M ;
HOLLY, FW ;
VEBER, DF .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (18) :3101-3105
[5]   REMOVAL OF BENZYL-TYPE PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH FORMIC-ACID [J].
ELAMIN, B ;
ANANTHARAMAIAH, GM ;
ROYER, GP ;
MEANS, GE .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (19) :3442-3444
[6]   NEW SYNTHETIC ROUTE TO N,N'-DIAMINOHYDANTOINS FROM HYDRAZIDO PYRIDINIUM SALTS [J].
FLORAC, C ;
LEGREL, P ;
BAUDYFLOCH, M ;
ROBERT, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (05) :1143-1146
[7]  
GANTE J, 1989, SYNTHESIS-STUTTGART, P405
[8]  
GANTE J, 1994, LIEBIGS ANN CHEM, P1231
[9]   Production of ring-substituted D-phenylglycines by microbial or enzymatic hydrolysis/deracemisation of the corresponding DL-hydantoins [J].
Garcia, MJ ;
Azerad, R .
TETRAHEDRON-ASYMMETRY, 1997, 8 (01) :85-92
[10]  
GY L, 1998, J MED CHEM, V41, P483