A NOVEL ASYMMETRIC-SYNTHESIS OF ATROPISOMERIC 6-ARYL PYRAZINONES VIA AN UNUSUAL CHIRALITY TRANSFER PROCESS - NEW CHIRAL LIGANDS FOR THE GABA(A) CHLORIDE IONOPHORE COMPLEX

被引：9

作者：

TULINSKY, J ^{[1
]}

MIZSAK, SA ^{[1
]}

WATT, W ^{[1
]}

DOLAK, LA ^{[1
]}

JUDGE, T ^{[1
]}

GAMMILL, RB ^{[1
]}

机构：

[1] UPJOHN CO, UPJOHN LABS, KALAMAZOO, MI 49001 USA

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 12期

关键词：

D O I：

10.1016/0040-4039(95)00216-Y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclization of (S,S)-alpha-[(1-phenylethyl)amino]-alpha-(2-iodophenyl)acetonitrile 3a with (COCl)(2) in toluene or chlorobenzene afforded the atropisomeric pyrazinone (aS,S) 6-(2-alpha-iodophenyl)-3,5-dichloro-1-(1-phenylethyl)-2(1H)-pyrazinone 7a in 57% yield. With smaller ortho substituents, mixtures of atropisomers were obtained. Stereochemical assignments were made via X-Ray and NOE experiments.

引用

页码：2017 / 2020

页数：4

共 14 条

[1] THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].