Nucleophilic vinylic substitutions of (E)- and (Z)-ethyl 3-aryl-3-chloro-2-cyanopropenoates with primary and secondary amines

被引:6
作者
Jalander, LF
Lonnqvist, JE
机构
[1] Department of Organic Chemistry, Åbo Akademi, Fin-20500 Åbo
关键词
D O I
10.1080/00397919608003764
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Some new (Z)-ethyl 3-amino-3-aryl-2-cyanopropenoates have been prepared in good yields by reacting (E)- and (Z)-ethyl 3-aryl-3-chloro-2-cyanopropenoates with primary and secondary amines. The (Z)-isomers were exclusively formed although the starting material consisted of a mixture of (E)- and (Z)-isomers (approximate to 1:1)
引用
收藏
页码:3549 / 3557
页数:9
相关论文
共 10 条
[1]   KINETICS OF REACTIONS OF THIOLATE IONS WITH ALPHA-NITRO BETA-SUBSTITUTED STILBENES IN 50-PERCENT ME2SO-50-PERCENT WATER - OBSERVATION OF THE INTERMEDIATE IN NUCLEOPHILIC VINYLIC SUBSTITUTION-REACTIONS [J].
BERNASCONI, CF ;
FASSBERG, J ;
KILLION, RB ;
RAPPOPORT, Z .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3169-3177
[2]  
BERNASCONI CF, 1989, J AM CHEM SOC, V111, P6962
[3]  
BERNASCONI CF, 1995, J AM CHEM SOS, V115, P1703
[4]  
BREITMAIER E, 1993, STRUCTURE ELUCIDATIO, P62
[5]  
DAMOW A, 1958, CHEM BER, V91, P1830
[6]   STUDIES ON GEOMETRIC ISOMERISM BY NUCLEAR MAGNETIC RESONANCE .1. STEREOCHEMISTRY OF ALPHA-CYANO--BETA-ALKOXY-BETA-ALKYLACRYLIC ESTERS [J].
HAYASHI, T ;
HORI, I ;
BABA, H ;
MIDORIKA.H .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (03) :695-&
[7]   STUDIES ON GEOMETRIC ISOMERISM BY NUCLEAR MAGNETIC RESONANCE .4. STRUCTURE OF ALPHA-CYANO-BETA-AMINO-BETA-ALKYLACRYLIC ESTERS [J].
HAYASHI, T ;
HORI, I ;
BABA, H ;
MIDORIKA.H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (09) :2160-+
[8]   VINYLIC NONIONIC SUBSTITUTIONS OF ETHYL (E)-3-CHLORO-2-CYANO-3-PHENYLPROPENOATE AND (Z)-3-CHLORO-2-CYANO-3-PHENYLPROPENOATE BY ALCOHOLS [J].
JALANDER, LF .
SYNTHETIC COMMUNICATIONS, 1993, 23 (16) :2293-2302
[9]  
Kessler H., 1970, ANGEW CHEM, V82, P237
[10]   REACTIONS OF ENAMINONITRILES WITH PHOSGENE - SYNTHESIS OF ENAMINOCARBOXYLIC ACID-CHLORIDES [J].
OHOKA, M ;
ASADA, K ;
YANAGIDA, S ;
OKAHARA, M ;
KOMORI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (13) :2287-2290