Copper-Catalyzed Ritter-Type Reaction of Unactivated Alkenes with Dichloramine-T

被引：27

作者：

Abe, Takumi ^{[1
]}

Takeda, Hiroyuki ^{[1
]}

Miwa, Yoshihisa ^{[2
]}

Yamada, Koji ^{[1
]}

Yanada, Reiko ^{[2
]}

Ishikura, Minoru ^{[1
]}

机构：

[1] Hlth Sci Univ Hokkaido, Fac Pharmaceut Sci, Ishikari, Hokkaido 0610293, Japan

[2] Hiroshima Int Univ, Fac Pharmaceut Sci, Hiroshima 7370112, Japan

来源：

HELVETICA CHIMICA ACTA | 2010年 / 93卷 / 02期

关键词：

STEREOSELECTIVE AMINOHALOGENATION; ELECTROPHILIC DIAMINATION; CINNAMIC ESTERS; NITRILES;

D O I：

10.1002/hlca.200900214

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

It was shown that dichloramine-T (1) reacted with cyclohexene in acetonitrile to give N'-(2-chlorocyclohexyl) amidine 2a and N-(2-chlorocyclohexyl)acetamide (3) via the competitive addition of acetonitrile and N-chloro-N-tosylamino anion to cyclohexenechloronium ion. This reaction can be catalyzed by Cu(OAc)(2), primarily affording 2a. Furthermore, the resulting 2a can be cyclized to benzimidazol 14a in good yield by treating with KOH in dioxane.

引用

页码：233 / 241

页数：9