OCCURRENCE OF AN SN(ANRORC) MECHANISM IN THE CHICHIBABIN AMINATION OF 4-PHENYLPYRIMIDINE .78.

被引:20
作者
BREUKER, K [1 ]
VANDERPLAS, HC [1 ]
机构
[1] AGR UNIV,ORGAN CHEM LAB,NL-6703 BC WAGENINGEN,NETHERLANDS
关键词
D O I
10.1021/jo00393a043
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oil treatment of 4-phenylpyrimidine with potassium amide in liquid ammonia, a mixture of 6-amino-4-phenylpyrirnidine and 2-amino-4-phenylpyrimidine is obtained. It was proven that in the formation of the 2-amino compound the pyrimidine ring is opened but that in the formation of the 6-amino compound no ring opening is involved, 1H and 13C NMR spectroscopy gave evidence for formation of two σ adducts between the amide ion and 4-phenylpyrimidine, i.e., the 6-amino-1(or 3),6-dihydropyrimidinide ion and the 2-amino-1(or 3),2-dihydropyrimidinide ion. © 1979, American Chemical Society. All rights reserved.
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页码:4677 / 4680
页数:4
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