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

页码：3065 / 3072

页数：8

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