Aroylation of fused pyrimidines; Synthesis of 4-aroylfuro[2,3-d]-, 4-aroylthieno[2,3-d]-, and 4-aroylisoxazolo[5,4-d]pyrimidines

被引:17
作者
Miyashita, A [1 ]
Obae, K [1 ]
Suzuki, Y [1 ]
Oishi, E [1 ]
Iwamoto, K [1 ]
Higashino, T [1 ]
机构
[1] UNIV SHIZUOKA,DIV ENVIRONM HLTH SCI,GRAD SCH NUTR & ENVIRONM SCI,SHIZUOKA 422,JAPAN
关键词
D O I
10.3987/COM-97-7914
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-Aroylfuro[2,3-d]-(4), 4-aroylthieno[2,3-d]-(7 and 8), and 4-aroylisoxazolo[5,4-d]pyrimidines (13) were synthesized by aroylation of the fused chloro-(3a and 12) or bromopyrimidines (3b, 5, and 6) with arenecarbaldehydes (2) catalyzed by an imidazolium salt (1a). The fused aroylpyrimidines (4 and 7) were also synthesized by oxidative decyanation of alpha-phenylheteroareneacetonitriles (10 and 11).
引用
收藏
页码:2159 / 2173
页数:15
相关论文
共 29 条
[1]  
Brown D. J., 1984, Comprehensive Heterocyclic Chemistry, V1, P57
[2]  
Cheng C C, 1969, Prog Med Chem, V6, P67
[3]  
DONETTI A, 1980, SYNTHESIS-STUTTGART, P1009
[4]   HETEROCYCLEN AUS CH-ACIDEN NITRILEN .9. UBER DIE REAKTION VON ALPHA-HYDROXY-KETONEN MIT MALODINITRIL [J].
GEWALD, K .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (03) :1002-&
[5]   2-AMINO-THIOPHENE AUS METHYLENAKTIVEN NITRILEN CARBONYLVERBINDUNGEN UND SCHWEFEL [J].
GEWALD, K ;
SCHINKE, E ;
BOTTCHER, H .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (01) :94-&
[6]   A NEW SYNTHESIS OF ARYL HETARYL KETONES VIA SRN1 REACTIONS OF HALOGENATED HETEROCYCLES WITH POTASSIOPHENYLACETONITRILE FOLLOWED BY PHASE-TRANSFER CATALYZED DECYANATION [1A-C] [J].
HERMANN, CKF ;
SACHDEVA, YP ;
WOLFE, JF .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (04) :1061-1065
[7]  
HITCHINGS GH, 1950, J BIOL CHEM, V183, P1
[8]  
HITCHINGS GH, 1948, J BIOL CHEM, V174, P765
[9]  
Janda M., 1976, ANGEW CHEM, V88, P475
[10]  
MATSUDA A, 1984, SYNTHESIS-STUTTGART, P963