Thieno[3,4-b]pyrazines:: Synthesis, structure, and reactivity

被引:128
作者
Kenning, DD [1 ]
Mitchell, KA [1 ]
Calhoun, TR [1 ]
Funfar, MR [1 ]
Sattler, DJ [1 ]
Rasmussen, SC [1 ]
机构
[1] N Dakota State Univ, Dept Chem, Fargo, ND 58105 USA
关键词
D O I
10.1021/jo0262255
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general synthetic route has been developed for the efficient preparation of 2,3-disubstituted thieno[3,4-b]pyrazines. These methods eliminate problems in the preparation of the precursor 3,4-diaminothiophene and utilize alpha-diones prepared through the reaction of the appropriate organocuprates with oxalyl chloride. This combination allows the convenient preparation of thieno [3,4-b] pyrazine and its 2,3-disubstituted analogues (where substituent = methyl, hexyl, octyl, decyl, dodecyl, and phenyl) in high yield. Characterization of the structure and reactivity of this class of compounds is also described, including the results of structural, electrochemical, and pK(a) studies.
引用
收藏
页码:9073 / 9076
页数:4
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