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.
引用
收藏
页码:4677 / 4680
页数:4
相关论文
共 15 条
[1]   The direct introduction of the amino group into the aromatic and heterocyclic nucleus III Further observations concerning the action of the alkali amides on quinoline and isoquinoline [J].
Bergstrom, FW .
JOURNAL OF ORGANIC CHEMISTRY, 1937, 2 (05) :411-430
[2]   CHICHIBABIN REACTION OF PURINES WITH POTASSIUM-AMIDE IN LIQUID-AMMONIA [J].
KOS, NJ ;
VANDERPLAS, HC ;
VANVELDHUIZEN, B .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (18) :3140-3143
[3]   NUCLEAR MAGNETIC-RESONANCE DATA OF PYRIDO[2,3-B]PYRAZINES AND THEIR SIGMA-ADDUCTS WITH AMIDE ION AND WATER [J].
NAGEL, A ;
VANDERPLAS, HC ;
GEURTSEN, G ;
VANVELDHUIZEN, A .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1979, 16 (02) :301-304
[4]  
NAGEL A, 1975, CHEM PHARM BULL, V23, P2678
[5]  
NAGEL A, 1977, HETEROCYCLES, V7, P205
[6]  
OOSTVEEN EA, 1974, RECL TRAV CHIM PAY B, V93, P114
[7]  
RASMUSSEN CAH, 1978, TETRAHEDRON LETT, P3841
[8]   INVESTIGATIONS INTO CINE-AMINATION OF 4-SUBSTITUTED-5-BROMOPYRIMIDINES BY POTASSIUM-AMIDE IN LIQUID-AMMONIA .70. [J].
RASMUSSEN, CAH ;
VANDERPLAS, HC ;
GROTENHUIS, P ;
KOUDIJS, A .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1978, 15 (07) :1121-1125
[9]  
SHEPHERD RG, 1965, ADV HETEROCYCL CHEM, V4, P291
[10]  
SIMIG G, 1976, RECL TRAV CHIM PAY B, V95, P125