FECL3-CATALYZED CONJUGATE ADDITION OF SECONDARY-AMINES, IMIDAZOLE AND PYRAZOLE TO METHYL 2-ACETAMIDOACRYLATE - PREPARATION OF BETA-DIALKYLAMINO-ALPHA-ALANINE AND BETA-(N-HETEROARYL)-ALPHA-ALANINE DERIVATIVES

被引:65
作者
PEREZ, M [1 ]
PLEIXATS, R [1 ]
机构
[1] UNIV AUTONOMA BARCELONA,DEPT CHEM,E-08193 BARCELONA,SPAIN
关键词
D O I
10.1016/0040-4020(95)00446-F
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
beta-Dialkylamino-alpha-alanine and beta-(N-heteroaryl)-alpha-alanine derivatives are obtained by conjugate addition of nitrogen based nucleophiles (cyclic and acyclic secondary amines, imidazole and pirazole) to methyl 2-acetamidoacrylate, 1, under iron(III) chloride catalysis.
引用
收藏
页码:8355 / 8362
页数:8
相关论文
共 27 条
[1]   SYNTHESIS OF OPTICALLY PURE ALPHA-AMINO-ACIDS VIA SALTS OF ALPHA-AMINO-BETA-PROPIOLACTONE [J].
ARNOLD, LD ;
MAY, RG ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2237-2241
[2]   CONVERSION OF SERINE BETA-LACTONES TO CHIRAL ALPHA-AMINO-ACIDS BY COPPER-CONTAINING ORGANOLITHIUM AND ORGANOMAGNESIUM REAGENTS [J].
ARNOLD, LD ;
DROVER, JCG ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (15) :4649-4659
[3]   CONVERSION OF SERINE TO STEREOCHEMICALLY PURE BETA-SUBSTITUTED ALPHA-AMINO-ACIDS VIA BETA-LACTONES [J].
ARNOLD, LD ;
KALANTAR, TH ;
VEDERAS, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7105-7109
[4]   SYNTHESIS AND PMR PROPERTIES OF SOME DEHYDROALANINE DERIVATIVES [J].
ASQUITH, RS ;
CARTHEW, P .
TETRAHEDRON, 1972, 28 (18) :4769-&
[5]  
ASQUITH RS, 1977, TETRAHEDRON, V133, P1633
[6]   SYNTHESIS OF L-BETA-(ISOXAZOLIN-5-ONE-2-YL)-ALANINE - A NOVEL METHOD FOR THE SYNTHESIS OF N-SUBSTITUTED 3,4-UNSUBSTITUTED ISOXAZOLIN-5-ONES [J].
BALDWIN, JE ;
ADLINGTON, RM ;
BIRCH, DJ .
TETRAHEDRON LETTERS, 1985, 26 (48) :5931-5934
[7]  
BALDWIN JE, 1994, TETRAHEDRON, V50, P5049
[8]   ASYMMETRIC-SYNTHESIS OF BETA-SUBSTITUTED ALPHA-AMINO-ACIDS VIA A CHIRAL NI-II COMPLEX OF DEHYDROALANINE [J].
BELOKON, YN ;
SAGYAN, AS ;
DJAMGARYAN, SM ;
BAKHMUTOV, VI ;
BELIKOV, VM .
TETRAHEDRON, 1988, 44 (17) :5507-5514
[9]   CONVERSION OF BETA-CHLORO-L-ALANINE TO ALPHA-CARBOBENZOXY-DL-DIAMINOPROPIONIC ACID [J].
BENOITON, L .
CANADIAN JOURNAL OF CHEMISTRY, 1968, 46 (09) :1549-&
[10]   CATALYSIS OF THE SPECIFIC MICHAEL ADDITION - THE EXAMPLE OF ACRYLATE ACCEPTORS [J].
CABRAL, J ;
LASZLO, P ;
MAHE, L ;
MONTAUFIER, MT ;
RANDRIAMAHEFA, SL .
TETRAHEDRON LETTERS, 1989, 30 (30) :3969-3972