Solution-phase parallel synthesis of 4,6-diaryl-pyrimidine-2-ylamines and 2-amino-5,5-disubstituted-3,5-dihydro-imidazol-4-ones via a rearrangement

被引:62
作者
Varga, L [1 ]
Nagy, T [1 ]
Kövesdi, I [1 ]
Benet-Buchholz, J [1 ]
Dormán, G [1 ]
Ürge, L [1 ]
Darvas, F [1 ]
机构
[1] ComGenex Inc, H-1388 Budapest 62, Hungary
关键词
chalcon; 2-amino-pyrimidine; 2-amino-5-benzyl-5-phenyl-3,5-dihydro-imidazol-4-one;
D O I
10.1016/S0040-4020(02)01560-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of chalcones and guanidine was investigated in the presence of an oxidizing agent. Depending on the order of the addition either a 4,6-diaryl-pyriniidine-2-ylamine or 2-aniino-5,5-disubstituted-3,5-dihydro-imidazol-4-one was obtained. The structures of the imidazolinones were elucidated by NMR spectroscopy and X-ray crystallography and for its formation a mechanism was proposed. (C) 2003 Published by Elsevier Science Ltd.
引用
收藏
页码:655 / 662
页数:8
相关论文
共 17 条
[1]   REACTION OF ALPHA,BETA-UNSATURATED KETONES WITH GUANIDINE - SUBSTITUENT EFFECTS ON THE PROTONATION CONSTANTS OF 2-AMINO-4,6-DIARYLPYRIMIDINES [J].
ALHAJJAR, FH ;
SABRI, SS .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (05) :1087-1092
[2]   ACETYLINIC KETONES .2. REACTION OF ACETYLENIC KETONES WITH NUCLEOPHILIC NITROGEN-COMPOUNDS [J].
BADDAR, FG ;
ALHAJJAR, FH ;
ELRAYYES, NR .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1976, 13 (02) :257-268
[3]   STUDIES IN CHEMOTHERAPY .12. SOME SULFANILAMIDOHETEROCYCLES [J].
CLARK, JH ;
ENGLISH, JP ;
WINNEK, PS ;
MARSON, HW ;
COLE, QP ;
CLAPP, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (01) :96-99
[4]   Combinatorial chemistry. Facing the challenge of chemical genomics [J].
Darvas, F ;
Dorman, G ;
Urge, L ;
Szabo, I ;
Ronai, Z ;
Sasvari-Szekely, M .
PURE AND APPLIED CHEMISTRY, 2001, 73 (09) :1487-1498
[5]  
DARVAS F, 1997, HIGH THROUGHPUT SCRE, P223
[6]  
Darvas F., 2002, HDB COMBINATORIAL CH, P806
[7]   REACTION OF "1,3-DIARYL-2,3-DIBROMO-1-PROPANONES WITH UREA IN BASIC AND ACIDIC MEDIUM - SYNTHESIS OF PYRIMIDINE, IMIDAZOLINE AND IMIDAZOLIDINE DERIVATIVES [J].
DORA, EK ;
DASH, B ;
PANDA, CS .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (03) :691-696
[9]  
FURNISS BS, 1989, VOGELS TXB PRACTICAL, P1034
[10]  
JOERLANDER H, 1917, CHEM BER, V50, P1457