REACTION-MECHANISM BETWEEN PYRUVIC-ACID AND AROMATIC-AMINES

被引:4
|
作者
TAPIA, I [1 ]
ALCAZAR, V [1 ]
MORAN, JR [1 ]
GRANDE, M [1 ]
机构
[1] UNIV SALAMANCA, FAC CIENCIAS QUIM, DEPT ORGAN CHEM, E-37008 SALAMANCA, SPAIN
关键词
D O I
10.1246/bcsj.63.2408
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The formation of the condensation products obtained when pyruvic acid and aromatic amines are allowed to react, can be explained by condensation of one mole of the imine of pyruvic acid with one mole of the enamine isomer, either through the C atom or through the N atom, followed by elimination and lactonization to give a γ-lactone carboxylate or an azlactone carboxylate, which on decarboxylation give an iminobutanolide or an azlactone respectively. Aminolysis of these cyclic intermediates led to the formation of the final products. © 1990 The Chemical Society of Japan.
引用
收藏
页码:2408 / 2413
页数:6
相关论文
共 50 条
  • [1] REACTION OF PARA-NITROSODIMETHYLANILINE WITH PYRUVIC-ACID AND ITS DERIVATIVES .6. CONDENSATION OF PHENYLPYRUVIC ACID WITH PRIMARY AROMATIC-AMINES
    RUSE, M
    VULCU, R
    JEPAN, I
    [J]. MONATSHEFTE FUR CHEMIE, 1976, 107 (04): : 1007 - 1010
  • [2] THE REACTION OF PYRUVIC-ACID WITH AMINES AND AMINOESTERS REEXAMINED
    BRADAMANTE, S
    COLOMBO, S
    PAGANI, GA
    ROELENS, S
    [J]. HELVETICA CHIMICA ACTA, 1981, 64 (02) : 568 - 571
  • [3] A REEXAMINATION OF THE REACTION BETWEEN PYRUVIC-ACID AND ANILINE
    TAPIA, I
    ALCAZAR, V
    GRANDE, M
    MORAN, JR
    [J]. TETRAHEDRON, 1988, 44 (16) : 5113 - 5116
  • [4] REACTION-MECHANISM OF ACETYL HALIDES WITH AROMATIC-AMINES IN THE PRESENCE OF N-SUBSTITUTED IMIDAZOLES
    LAPSHIN, SA
    DADALI, VA
    LITVINENKO, LM
    SIMANENKO, YS
    [J]. ZHURNAL ORGANICHESKOI KHIMII, 1981, 17 (09): : 1938 - 1944
  • [5] REACTION OF PYRUVIC-ACID WITH NITROSOBENZENES
    URSIC, S
    VRCEK, V
    GABRICEVIC, M
    ZORC, B
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (04) : 296 - 298
  • [6] REACTION WITH PYRIDINIUM PYRUVIC-ACID ESTER
    WESTPHAL, G
    SCHEYBAL, A
    LIPKE, B
    WEBER, FG
    [J]. PHARMAZIE, 1976, 31 (11): : 770 - 773
  • [7] MECHANISM OF THE REACTION OF N-CHLOROSULFONAMIDES WITH AROMATIC-AMINES
    WHITE, WN
    WHITE, HS
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 199 : 259 - ORGN
  • [8] KINETICS AND MECHANISM OF THE REACTION OF AQUEOUS EUROPIUM(II) ION WITH PYRUVIC-ACID
    KONSTANTATOS, J
    VRACHNOUASTRA, E
    KATSAROS, N
    KATAKIS, D
    [J]. INORGANIC CHEMISTRY, 1982, 21 (01) : 122 - 126
  • [9] REACTION OF PHENYLIMINOETHOXALYLISOTHIOCYANATE WITH AROMATIC-AMINES
    LOZINSKII, MO
    SHIVANYUK, AF
    BODNAR, VN
    PELKIS, PS
    [J]. ZHURNAL ORGANICHESKOI KHIMII, 1975, 11 (09): : 1983 - 1984
  • [10] INITIATION MECHANISM OF REACTION OF AROMATIC-AMINES WITH CARBON-TETRACHLORIDE
    IWASAKI, T
    SAWADA, T
    OKUYAMA, M
    KAMADA, H
    [J]. PHOTOGRAPHIC SCIENCE AND ENGINEERING, 1978, 22 (06): : 312 - 315