Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines

被引：2
|
作者：
Hess, A. [1 ]
Guelen, H. C. [1 ]
Alandini, N. [1 ]
Mourati, A. [1 ]
Guersoy, Y. C. [1 ]
Knochel, P. [1 ]
机构：
[1] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13,Haus F, D-81377 Munich, Germany
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2022年 / 28卷 / 01期
关键词：
aryl nitriles; aryl oxazolines; cyanation; directed metalation; Grignard reagents; CATALYZED CYANATION; CONVENIENT SYNTHESIS; ORGANIC-CHEMISTRY; ELECTRON-RICH; TRANSFORMATION; METALATION; ARYLATION; ALDEHYDES; AMIDES; HETEROARENES;
D O I：
10.1002/chem.202103700
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A selective ortho,ortho'-functionalization of readily available aryl oxazolines by two successive magnesiations with sBu(2)Mg in toluene followed by trapping reactions with electrophiles, such as (hetero)aryl iodides or bromides, iodine, tosyl cyanide, ethyl cyanoformate or allylic bromides (39 examples, 62-99 % yield) is reported. Treatment of these aryl oxazolines with excess oxalyl chloride and catalytic amounts of DMF (50 degrees C, 4 h) provided the corresponding nitriles (36 examples, 73-99 % yield). Conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed.
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页数：5
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