HETEROARYLAMINATION AND HETEROARYLSULFIDATION OF 2-CHLORO-1-AZAAZULENES

被引：9
|
作者：
Yoshioka, Eiko [1 ,2 ]
Koizumi, Kazuya [1 ,2 ]
Yamazaki, Shinya [1 ,2 ]
Fujii, Hiroyuki [3 ]
Abe, Noritaka [1 ,2 ]
机构：
[1] Yamaguchi Univ, Fac Sci, Grad Sch Med, Yamaguchi 7538512, Japan
[2] Yamaguchi Univ, Fac Sci, Dept Biol & Chem, Yamaguchi 7538512, Japan
[3] Yamaguchi Univ, Ctr Sci Res, Yamaguchi 7538512, Japan
来源：
HETEROCYCLES | 2009年 / 78卷 / 12期
关键词：
Heteroarylamination; Heteroarylsulfidation; Bis(1-azaazulen-2-yl)amine; Bis(1-azaazulen-2-yl) Sulfide; SNAr Reaction; ARYL HALIDES; AMINATION;
D O I：
10.3987/COM-09-11806
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Heteroarylamination and heteroarylsulfidation of 2-chloro-1-azaazulenes (1) were investigated. Palladium catalyzed coupling of 2-amino-1-azaazulenes (2) with I underwent to give bis(1-azaazulen-2-yl)amine derivatives in good yields, but the reaction of 2-mercapto-1-azaazulenes (4) with I did not give good results in the same conditions. The reaction of 4 with I under basic conditions gave bis(1-azaazulen-2-yl) sulfide derivatives in good yields. Heteroarylamino-substitution was proceeded on the reaction of 4-amino-3-mercapto-4H-1,2,4-triazoles (6) with I in BuOH under reflux, whereas heteroarylsulfido-substitution was proceeded on the reaction of 6 with I in the presence of NaH in dioxane.
引用
收藏
页码：3065 / 3072
页数：8
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