Metalation of t-butyl sulfoxides, sulfones and sulfonamides of pyridazine and pyrazine. Metalation of diazines. XX

被引:19
|
作者
Turck, A [1 ]
Ple, N [1 ]
Pollet, P [1 ]
Queguiner, G [1 ]
机构
[1] INSA, IRCOF, Lab Chim Organ Fine & Heterocycl, UPRESA 6014, F-76131 Mt St Aignan, France
关键词
D O I
10.1002/jhet.5570350228
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the pyridazine series, the use of tert-butylsulfinyl and tert-butylsulfonyl as ortho directing groups for metalation has been tested. Various functionalized products were obtained in good yields. In the case of 3-tert-butylsulfinyl-6-methoxypyridazine the metalation was regioselective in ortho to the sulfinyl group. The metalation of 2-tert-butylsulfinyl and 2-tert-butylsulfonylpyrazine gave low to moderate yields. Synthesis of diazinesulfonamides were improved and the metalation of N-tert-butylsulfonamidopyrazine was achieved.
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收藏
页码:429 / 436
页数:8
相关论文
共 2 条
  • [1] Metalation of sulfoxides in the benzodiazine series.: Diazines.: Part 44
    Le Fur, N
    Mojovic, L
    Plé, N
    Turck, A
    Marsais, F
    [J]. TETRAHEDRON, 2005, 61 (37) : 8924 - 8931
  • [2] Synthesis of chiral diazine and pyridine sulfoxides.: Asymmetric induction by chiral sulfoxides in an "aromatic ortho-directed metalation-reaction with electrophiles sequence".: Diazines.: 24
    Pollet, P
    Turck, A
    Plé, N
    Quéguiner, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12): : 4512 - 4515