IMINOPHOSPHORANE-MEDIATED SYNTHESIS OF FUSED URACILS - A FACILE ONE-POT PREPARATION OF PYRIMIDO[4,5-D]PYRIMIDINE DERIVATIVES

被引:28
作者
MOLINA, P
VILAPLANA, MJ
PEREZ, J
机构
[1] Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Murcia, E-30071 Murcia, Campus de Espinardo
关键词
D O I
10.1016/S0040-4020(01)90083-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The aza Wittig-type reaction of iminophosphoranes 3, 5-[(N-Arylimino)methyl]-6-[(triphenylphosphoranylidene)amino]-1, 3-dimethyl uracils, with aromatic isocyanates leads to the functionalized pyrimido[4,5-d]pyrimidines 4. Iminophosphoranes 5, prepared from 3 by selective reduction with sodium borohydride, undergo dihydropyrimido annelation by reaction with isocyanates to give 7-amino-6-aryl-1,3-dimethyl-1,2,3,4,5,6-hexahydropyrimido[4,5-d]pyrimidines 6. © 1990.
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收藏
页码:7855 / 7864
页数:10
相关论文
共 22 条
[1]   PTERIDINE STUDIES .39. PTERIDINES UNSUBSTITUTED IN 4-POSITION - A NEW SYNTHESIS FROM PYRAZINES, VIA 3,4-DIHYDROPTERIDINES [J].
ALBERT, A ;
OHTA, K .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (11) :1540-&
[2]   ANNELATION OF A PYRIMIDINE RING TO AN EXISTING RING [J].
ALBERT, A .
ADVANCES IN HETEROCYCLIC CHEMISTRY, 1982, 32 :1-81
[3]   BOTH 2',3'-DIDEOXYTHYMIDINE AND ITS 2',3'-UNSATURATED DERIVATIVE (2',3'-DI-DEOXYTHYMIDINENE) ARE POTENT AND SELECTIVE INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS-REPLICATION INVITRO [J].
BABA, M ;
PAUWELS, R ;
HERDEWIJN, P ;
DECLERCQ, E ;
DESMYTER, J ;
VANDEPUTTE, M .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1987, 142 (01) :128-134
[4]   SYNTHESIS OF 2H-1,3-OXAZIN-2-ONES [J].
BAYDAR, AE ;
BOYD, GV .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :718-719
[5]   SYNTHESES IN HETEROCYCLIC SERIES .11. SYNTHESES OF PYRIDO(2,3-D)-AND PYRIMIDO(4,5-D)PYRIMIDIENE-THIOUREA AND SYNTHESIS OF (2-14C)-N,N'-ETHNES . A KETIMINE-ENAMINE TAUTOMERISM [J].
BREDERECK, H ;
SIMCHEN, G ;
WAHL, R ;
EFFENBER.F .
CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (02) :512-+
[6]  
Brown DJ, 1984, COMPREHENSIVE HETERO, V3, P57
[7]  
Clercq E. D., 1988, J MED CHEM, V29, P1561
[8]  
Clercq E. D., 1986, ANTICANCER RES, V6, P549
[9]   SYNTHESIS OF ISOCARBOSTYRILS AND 1-CHLOROISOQUINOLINES [J].
ELOY, F ;
DERYCKER.A .
HELVETICA CHIMICA ACTA, 1969, 52 (06) :1755-+
[10]  
HEIDELBERGER C, 1963, CANCER RES, V23, P1226