AMIDOALKYLATION OF AROMATICS WITH GLYOXYLIC ACID-GAMMA-LACTAM ADDUCTS - 2-PYRROLIDINONE, PYROGLUTAMIC ACID AMIDE AND ESTER

被引：19

作者：

ROTH, E

ALTMAN, J

KAPON, M

BENISHAI, D

机构：

[1] Department of Chemistry, Technion - Israel Institute of Technology, Technion City, Haifa

来源：

TETRAHEDRON | 1995年 / 51卷 / 03期

关键词：

D O I：

10.1016/0040-4020(94)00952-Q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A glyoxylic acid-2-pyrrolidinone adduct leads to N-acyliminium-ion induced intermolecular electrophilic aromatic substitution yielding nitrogen-substituted phenylglycine derivatives, whereas the benzylamide of glyoxylic acid-2-pyrrolidinone adduct undergoes intramolecular amidoalkylation to give an isoquinolone type compound. High stereospecifity and enantioselectivity was observed in intermolecular amidoalkylation of benzene using glyoxylic acid-S-pyroglutamic acid ester or amide adducts.

引用

收藏

页码：801 / 810

页数：10

相关论文

共 39 条

[1]

ANFINSEN CB, 1981, ADV PROTEIN CHEM, V34, P172

[2] GENERATION OF ALPHA-ACETOXYGLYCINE RESIDUES WITHIN PEPTIDE CHAINS - A NEW STRATEGY FOR THE MODIFICATION OF OLIGOPEPTIDES [J].

APITZ, G ;

JAGER, M ;

JAROCH, S ;

KRATZEL, M ;

SCHAFFELER, L ;

STEGLICH, W .

TETRAHEDRON, 1993, 49 (36) :8223-8232

[3] NEW SYNTHESIS OF N-ACYL AROMATIC ALPHA-AMINO-ACIDS - AMIDOALKYLATION OF AROMATIC-COMPOUNDS WITH GLYOXYLIC-ACID DERIVATIVES [J].

BENISHAI, D ;

SATATI, I ;

BERLER, Z .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (09) :349-350

[4] NEW SYNTHESIS OF N-ACYL AROMATIC ALPHA-AMINO-ACIDS - AMIDOALKYLATION OF AROMATIC AND HETEROCYCLIC-COMPOUNDS WITH GLYOXYLIC-ACID DERIVATIVES [J].

BENISHAI, D ;

SATATY, I ;

BERNSTEIN, Z .

TETRAHEDRON, 1976, 32 (13) :1571-1573

[5] INTRA VS INTERMOLECULAR AMIDOALKYLATION OF AROMATICS [J].

BENISHAI, D ;

SATATY, I ;

PELED, N ;

GOLDSHARE, R .

TETRAHEDRON, 1987, 43 (02) :439-450

[6] INTRAMOLECULAR AMIDOALKYLATION OF AROMATICS .2. SYNTHESIS OF CONFORMATIONALLY RESTRICTED BRIDGED PEPTIDES ANALOGS OF PHG-GLY OR GLY-PHG [J].

BENISHAI, D ;

MCMURRAY, AR .

TETRAHEDRON, 1993, 49 (29) :6399-6410

[7] SYNTHESIS OF PARA-SUBSTITUTED D,L-PHENYLGLYCINES BY AMIDOALKYLATION OF BENZYLCHLORIDE AND N-BENZYLBENZAMIDE [J].

BENISHAI, D ;

ALTMAN, J ;

PELED, N .

TETRAHEDRON, 1977, 33 (20) :2715-2717

[8]

BOULANGER A, 1994, TETRAHEDRON LETT, V25, P4345

[9] PRIMARY STRUCTURE OF OVINE HYPOTHALAMIC LUTEINIZING HORMONE-RELEASING FACTOR (LRF) [J].

BURGUS, R ;

BUTCHER, M ;

AMOSS, M ;

BLACKWELL, R ;

VALE, W ;

LING, N ;

RIVIER, J ;

MONAHAN, M ;

FELLOWS, R ;

GUILLEMIN, R .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1972, 69 (01) :278-+

[10]

DELASZLO SE, 1992, J MED CHEM, V35, P883

← 1 2 3 4 →