REGIOSPECIFIC ELECTROPHILIC SUBSTITUTION OF AMINOQUINAZOLINONES - DIRECTED LITHIATION OF 3-(PIVALOYLAMINO)-2-METHYLQUINAZOLIN-4(3H)-ONES AND 3-(ACETYLAMINO)-2-METHYLQUINAZOLIN-4(3H)-ONES

被引：48
|
作者：
SMITH, K [1 ]
ELHITI, GA [1 ]
ABDO, MA [1 ]
ABDELMEGEED, MF [1 ]
机构：
[1] TANTA UNIV,FAC SCI,DEPT CHEM,TANTA,EGYPT
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 08期
关键词：
D O I：
10.1039/p19950001029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The 2-methyl group in 3-(pivaloylamino)- and in 3-(acetylamino)-2-methylquinazolin-4(3H)-ones has been lithiated with butyllithium. The lithium reagents thus obtained react with a variety of electrophiles (benzophenone, methyl iodide, D2O, cyclohexanone, acetophenone, phenyl isocyanate) to give the corresponding substituted derivatives in very good yields. The amide group has been cleaved in good yield under basic conditions for one model case to provide convenient access to 3-amino-2-ethylquinazolin-4(3H)-one. The NMR spectra of the 2-substituted 3-acylaminoquinazolin-4(3H)-ones show diastereotopism of the CH2 group at position 2.
引用
收藏
页码：1029 / 1033
页数：5
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