UNUSUALLY FACILE RING-OPENING OF 5-ALKOXYOXAZOLES - APPLICATION TO THE SYNTHESIS OF DIMETHOXY-ALPHA-METHYLDOPA

被引:34
作者
JACOBI, PA
UENG, S
CARR, D
机构
[1] Hall-Atwater Laboratories, Wesleyan University, Middletown
关键词
D O I
10.1021/jo01326a039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the presence of n-BuLi, 5-alkoxyoxazoles undergo an unusually facile ring-opening reaction leading directly to lithiated isocyanoacetic acid derivatives, which in turn are versatile intermediates for the preparation of a variety of heterocyclic systems and amino acid derivatives. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:2042 / 2044
页数:3
相关论文
共 23 条
[1]   MASS SPECTRA OF SOME ALKYL AND ARYL OXAZOLES [J].
BOWIE, JH ;
DONAGHUE, PF ;
RODDA, HJ ;
COOKS, RG ;
WILLIAMS, DH .
ORGANIC MASS SPECTROMETRY, 1968, 1 (01) :13-&
[2]   AN EFFICIENT SYNTHESIS OF CIS-JASMONE [J].
BUCHI, G ;
WUEST, H .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (03) :977-&
[3]   SYNTHESIS OF PYRIDOXINE BY DIELS-ALDER REACTIONS WITH 4-METHYL-5-ALKOXY OXAZOLES [J].
FIRESTONE, RA ;
HARRIS, EE ;
REUTER, W .
TETRAHEDRON, 1967, 23 (02) :943-+
[4]   NOVEL SYNTHESIS OF L-(-)-ALPHA-METHYL-3,4-DIMETHOXYPHENYLALANINE [J].
FRETER, K ;
GOTZ, M ;
GROZINGER, K .
JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (10) :1072-+
[5]  
Grigg R., 1970, J CHEM SOC C, P552
[6]  
GRONOWITZ S, 1961, ARK KEMI, V17, P165
[7]   Synthetical experiments in the isoquinoline group. Part II. [J].
Haworth, RD ;
Perkin, WH ;
Rankin, J .
JOURNAL OF THE CHEMICAL SOCIETY, 1925, 127 :1444-1448
[8]   ALPHA-METALATED ISOCYANIDES IN ORGANIC SYNTHESIS [J].
HOPPE, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1974, 13 (12) :789-804
[9]   BIS HETEROANNULATION .1. MODEL STUDIES IN SYNTHESIS OF HIGHLY OXYGENATED SESQUITERPENES [J].
JACOBI, PA ;
CRAIG, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (24) :7748-7750
[10]  
KOOL M, 1978, TETRAHEDRON LETT, P1873