ONE-POT SYNTHESIS OF N-(2-HETEROARYL)-ALPHA-AMINO ESTERS BY THE REGIOSPECIFIC 2-N-(ALPHA-ALKOXYCARBONYL)ALKYLATION OF 2-AMINOAZINES AND 2-AMINOAZOLES WITH GLYOXALS AND ALCOHOLS PROMOTED BY PERCHLORIC-ACID

被引:12
作者
ALCAIDE, B
PLUMET, J
SIERRA, MA
机构
[1] Departamento de Quimica Organica I, Facultad de Quimica, Universidad Complutense
关键词
D O I
10.1021/jo00297a033
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Amino heterocycles, including pyridine, diazine, andd azole derivatives, are readily converted into N-(2-heteroaryl)-α-amino esters 4 in a one-pot sequence by reaction with glyoxals and alcohols in the presence of perchloric acid. In addition, the corresponding a-amino acids 5 are quantitatively obtained by acidic hydrolysis of compounds 4. © 1990, American Chemical Society. All rights reserved.
引用
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页码:3143 / 3147
页数:5
相关论文
共 22 条
[1]   THE REACTION OF ALPHA-DIKETONES WITH PRIMARY HETEROAROMATIC AMINES - SYNTHESIS AND REACTIONS OF IMIDAZO[1,2-A]PYRIDIN-3(2H)-ONES AND NORMAL-HETEROARYL ALPHA-IMINOKETONES [J].
ALCAIDE, B ;
PLUMET, J ;
SIERRA, MA .
TETRAHEDRON, 1989, 45 (21) :6841-6856
[2]   REACTION OF ARYLGLYOXALS WITH 2-AMINO HETEROCYCLES [J].
ALCAIDE, B ;
PLUMET, J ;
SIERRA, MA ;
VICENT, C .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (24) :5763-5768
[3]   IMIDAZO[1,2-B]PYRIDAZINES AND AN IMIDAZO[1,2-A]PYRAZINE FROM PYRIDAZIN-AMINES AND PYRAZIN-AMINES [J].
BARLIN, GB ;
BROWN, DJ ;
KADUNC, Z ;
PETRIC, A ;
STANOVNIK, B ;
TISLER, M .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1983, 36 (06) :1215-1220
[4]  
Barrett G.C., 1985, CHEM BIOCH AMINO ACI, P354
[5]   N-PHENYLATION OF AMINO-ACID DERIVATIVES [J].
BARTON, DHR ;
FINET, JP ;
KHAMSI, J .
TETRAHEDRON LETTERS, 1989, 30 (08) :937-940
[6]   MESO-IONIC COMPOUNDS DERIVED FROM PYRIDINO(1'-2'-1-2)GLYOXALINE [J].
BRISTOW, NW ;
CHARLTON, PT ;
PEAK, DA ;
SHORT, WF .
JOURNAL OF THE CHEMICAL SOCIETY, 1954, (FEB) :616-629
[7]   1,2,3-OXATHIAZOLIDINES - A NEW HETEROCYCLIC SYSTEM [J].
DEYRUP, JA ;
MOYER, CL .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (01) :175-&
[8]  
EFFENBERGER F, 1986, LIEBIGS ANN CHEM, P314
[9]  
FLOID MB, 1985, J ORG CHEM, V50, P5022
[10]  
GOTO T, 1968, TETRAHEDRON LETT, P3873