DIPHENYL (2,3-DIHYDRO-2-THIOXO-3-BENZOXAZOLYL)PHOSPHONATE - A NEW, REACTIVE CONDENSING AGENT FOR THE SYNTHESIS OF AMIDES, ESTERS, PEPTIDES, AND BETA-LACTAMS VIA CONDENSATION

被引:22
作者
UEDA, M
MORI, H
机构
[1] Dept. Materials Science/Engineering, Faculty of Engineering, Yamagata University
关键词
D O I
10.1246/bcsj.65.1636
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Diphenyl (2,3-dihydro-2-thioxo-3-benzoxazolyl)phosphonate (1) prepared from 2-benzoxazolethiol and diphenyl phosphorochloridate was proved to be a very useful condensing agent. A variety of amides, esters, and dipeptides were obtained in excellent yields. Furthermore, this reagent was successfully applied to the synthesis of beta-lactams from beta-amino acids.
引用
收藏
页码:1636 / 1641
页数:6
相关论文
共 22 条
[1]  
CASTROB, 1975, TETRAHEDRON LETT, P1219
[2]  
GANTE J, 1965, ANGEW CHEM, V77, P813
[3]  
Gross E., 1979, PEPTIDES, V1-9
[4]   EFFICIENT CONVERSION OF CARBOXYLIC-ACIDS INTO THIOL ESTERS [J].
KUNIEDA, T ;
ABE, Y ;
HIROBE, M .
CHEMISTRY LETTERS, 1981, (10) :1427-1428
[5]  
LOSSE G, 1964, LIEBIGS ANN CHEM, V678, P148
[6]  
OGLIARUSO MA, 1979, CHEM ACID DERIVATI 1, P474
[7]   A NOVEL REAGENT (N-SUCCINIMIDYL DIPHENYLPHOSPHATE) FOR SYNTHESIS OF ACTIVE ESTER AND PEPTIDE [J].
OGURA, H ;
NAGAI, S ;
TAKEDA, K .
TETRAHEDRON LETTERS, 1980, 21 (15) :1467-1468
[8]   N,N '-Carbonyldiimidazole, a new peptide forming Reagent [J].
Paul, Rolf ;
Anderson, George W. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (17) :4596-4600
[9]  
SCHMIDT U, 1988, SYNTHESIS-STUTTGART, P475
[10]  
SCHRODER E, 1964, LIEBIGS ANN CHEM, V673, P176