Metalation of diazines .17. Very hindered bases as new metalating agents; Improvement of regioselectivity for the metalation of 3-chloro-6-methoxypyridazine

被引:19
作者
Mojovic, L [1 ]
Turck, A [1 ]
Ple, N [1 ]
Dorsy, M [1 ]
Ndzi, B [1 ]
Queguiner, G [1 ]
机构
[1] INSA,IRCOF,LAB CHIM ORGAN FINE & HETEROCYCL,CNRS,URA 1429,F-76131 MONT ST AIGNAN,FRANCE
关键词
D O I
10.1016/0040-4020(96)00568-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The different factors governing the regioselectivity of the metalation of 3-chloro-6-methoxypyridazine with alkylamides were studied. Very hindered bases were used as new metalating agents and a very good regioselectivity was obtained. Copyright (C) 1996 Elsevier Science Ltd
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收藏
页码:10417 / 10426
页数:10
相关论文
共 17 条
[1]  
AUDEH CA, 1979, J CHEM RES SYNOP, P270
[2]   CHEMISTRY OF HINDERED AMINES - SYNTHESIS AND PROPERTIES OF DI-T-BUTYLAMINE AND RELATED COMPOUNDS [J].
BACK, TG ;
BARTON, DHR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (08) :924-927
[3]   SYNTHESIS OF DI-TERT-ALKYLAMINES [J].
COREY, EJ ;
GROSS, AW .
TETRAHEDRON LETTERS, 1984, 25 (05) :491-494
[4]  
COUTURE K, 1995, THESIS ROUEN
[5]   LITHIUM DIALKYLAMIDES - C-13 PARAMETERS AND SLOW PROTON-TRANSFER [J].
FRASER, RR ;
BAIGNEE, A ;
BRESSE, M ;
HATA, K .
TETRAHEDRON LETTERS, 1982, 23 (41) :4195-4198
[6]  
FRASER RR, 1984, J ORG CHEM, V49, P3442, DOI 10.1021/jo00192a059
[7]   LITHIUM 2,2,6,6-TETRAMETHYLPIPERIDIDE AND RELATED, STRONG, PROTON-SPECIFIC BASES - EVALUATION IN SYNTHESIS [J].
OLOFSON, RA ;
DOUGHERT.CM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :582-584
[8]   METALATION OF DIAZINES .10. FIRST HALOGEN MIGRATION DURING METALATION OF PYRIMIDINES UNUSUAL HALOGEN-LITHIUM EXCHANGE WITH LTMP - NEW SYNTHESIS OF LESHMANIACIDES [J].
PLE, N ;
TURCK, A ;
COUTURE, K ;
QUEGUINER, G .
TETRAHEDRON, 1994, 50 (34) :10299-10308
[9]   METALATION OF DIAZINES .5. SYNTHESIS OF ANALOGS OF BIOLOGICALLY-ACTIVE MOLECULES [J].
PLE, N ;
TURCK, A ;
BARDIN, F ;
QUEGUINER, G .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (02) :467-470
[10]  
STOWELL JC, 1974, SYNTHESIS-STUTTGART, V2, P127