THE TRANSFORMATIONS OF 4-HETEROARYLAMINOMETHYLENE-5(4H)-OXAZOLONES INTO DEHYDROPEPTIDE DERIVATIVES

被引:8
作者
ALJAZROZIC, M
SVETE, J
STANOVNIK, B
机构
[1] Faculty of Chemistry and Chemical Technology, University of Ljubljana, Ljubljana
关键词
D O I
10.1002/jhet.5570320533
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Phenyl-4-heteroarylaminomethylene-5(4H)-oxazolones 3, which were prepared from the corresponding N,N-dimethyl-N'-heteroarylformamidines 1 and hippuric acid 2 in acetic anhydride, react with amino acids giving dehydropeptide derivatives 4, 5, and 6 as products. Dehydration of N-protected peptides 7-10, containing glycine at the C-terminal, followed by the reaction with formamidines 1 gave 2-substituted-4-heteroarylaminomethylene-5(4H)-oxazolones 11-14.
引用
收藏
页码:1605 / 1611
页数:7
相关论文
共 10 条
[1]  
[Anonymous], 1993, PROG HETEROCYCL CHEM, DOI [DOI 10.1002/JHET.5570270247Z, 10.1002/jhet.5570270247z(]
[2]   A general procedure of the peptide synthesis. [J].
Bergmann, M ;
Zervas, L .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1932, 65 (07) :1192-1201
[3]   AN IMPROVED GENERAL-SYNTHESIS OF 4-ARYL-5-PYRIMIDINECARBOXYLATES [J].
BREAUX, EJ ;
ZWIKELMAIER, KE .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (01) :183-184
[4]  
Doherty David G., 1943, JOUR BIOL CHEM, V147, P617
[5]  
FISCHER E, 1905, BER CHEM GES, V38, P605
[6]   TRANSFORMATIONS OF HETEROCYCLIC N-OXIDES INTO DERIVATIVES OF ALPHA-HETEROARYL SUBSTITUTED ALPHA-AMINO-ACIDS AND DIPEPTIDES [J].
STANOVNIK, B ;
DROFENIK, I ;
TISLER, M .
HETEROCYCLES, 1987, 26 (07) :1805-1811
[7]   TRANSFORMATIONS OF N-HETEROARYLFORMAMIDINES INTO DERIVATIVES OF BETA-HETEROARYLAMINO-ALPHA,BETA-DEHYDRO-ALPHA-AMINO ACIDS, BETA-HETEROARYLAMINO-ALPHA-AMINO ACIDS, AND DIPEPTIDES [J].
STANOVNIK, B ;
SVETE, J ;
TISLER, M .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (06) :1809-1810
[8]   REACTIONS OF N-HETEROARYLFORMAMIDE OXIMES AND N-HETEROARYLACETAMIDE OXIMES WITH N,N-DIMETHYLFORMAMIDE DIMETHYL ACETAL - SYNTHESIS OF 2-METHYL-S-TRIAZOLO[1,5-CHI]AZINES AND N-METHYLCYANOAMINOAZINES [J].
STANOVNIK, B ;
STIMAC, A ;
TISLER, M ;
VERCEK, B .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (03) :577-583
[9]   TRANSFORMATION OF AMINES AND N-HETEROARYLFORMAMIDINES INTO ESTERS OF SUBSTITUTED BETA-AMINO-ALPHA,BETA-DEHYDRO-ALPHA-AMINO ACIDS [J].
STANOVNIK, B ;
SVETE, J ;
TISLER, M ;
ZORZ, L ;
HVALA, A ;
SIMONIC, I .
HETEROCYCLES, 1988, 27 (04) :903-909
[10]   THE SYNTHESIS OF BETA-HETEROARYLAMINO-ALPHA,BETA-DEHYDRO-ALPHA-AMINO ACID AND BETA-HETEROARYLAMINO-ALPHA-AMINO ACID-DERIVATIVES [J].
SVETE, J ;
STANOVNIK, B ;
TISLER, M ;
GOLIC, L ;
LEBAN, I .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (01) :145-153