A SIMPLE SYNTHESIS OF DELTA-2-OXAZOLINES, DELTA-2-OXAZINES, DELTA-2-THIAZOLINES AND 2-SUBSTITUTED BENZOXAZOLES

被引:194
作者
VORBRUGGEN, H
KROLIKIEWICZ, K
机构
[1] Research Laboratories, Schering AG
关键词
D O I
10.1016/0040-4020(93)80021-K
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carboxylic acids react readily at 0-degrees --> +24-degrees-C with amino alcohols, amino mercaptans and o-aminophenols in the presence of triphenylphosphine- or tributylphosphine dichloride (generated in situ from the reaction of the phosphines with hexachloroethane or CCl4) and triethylamine in acetonitrile to form the corresponding DELTA2-oxazolines, DELTA2-oxazines, DELTA2-thiazolines and 2-substituted benzoxazoles in one reaction step in yields of up to 80%.
引用
收藏
页码:9353 / 9372
页数:20
相关论文
共 70 条
[1]  
AABERG A, 1979, TETRAHEDRON LETT, P2263
[2]   STIMULTANEOUS ACTION OF AMMONIA (AMINES, IMINES) TOGETHER WITH CARBONTETRACHLORIDE ON PHOSPHINES .1. [J].
APPEL, R ;
KLEINSTU.R ;
ZIEHN, KD ;
KNOLL, F .
CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (11) :3631-&
[3]   CONVENIENT METHOD FOR PREPARATION OF DICHLOROPHOSPHORANES [J].
APPEL, R ;
SCHOLER, H .
CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (06) :2382-2384
[4]  
APPEL R, 1975, LIEBIGS ANN CHEM, P406
[5]   NEW AZIRIDINE SYNTHESIS [J].
APPEL, R ;
KLEINSTU.R .
CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (01) :5-12
[6]   TERTIARY PHOSPHANE-TETRACHLOROMETHANE, A VERSATILE REAGENT FOR CHLORINATION, DEHYDRATION, AND P-N LINKAGE [J].
APPEL, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1975, 14 (12) :801-811
[7]   ENANTIOSELECTIVE HYDROSILYLATION OF ACETOPHENONE WITH RHODIUM OXAZOLINES CATALYSTS [J].
BALAVOINE, G ;
CLINET, JC ;
LELLOUCHE, I .
TETRAHEDRON LETTERS, 1989, 30 (38) :5141-5144
[8]   AN EFFICIENT TOTAL SYNTHESIS OF AGROBACTIN AND ITS GALLIUM(III) CHELATE [J].
BERGERON, RJ ;
MCMANIS, JS ;
DIONIS, JB ;
GARLICH, JR .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (15) :2780-2782
[9]   1.3-DIPOLARE CYCLOADDITIONEN .11. DIE ANLAGERUNG DES AROMATISCHEN KETOCARBENS AUS 3.4.5.6-TETRACHLOR-BENZOL-2-DIAZO-1-OXID AN ALKENE [J].
BINSCH, G ;
KONIG, H ;
HUISGEN, R .
CHEMISCHE BERICHTE-RECUEIL, 1964, 97 (10) :2893-&
[10]  
BODOR N, 1981, Drugs of the Future, V6, P165