Synthesis of imidazoles through the copper-catalyzed cross-cycloaddition between two different isocyanides

被引：165

作者：

Kanazawa, Chikashi ^{[1
]}

Kamijo, Shin ^{[1
]}

Yamamoto, Yoshinori ^{[1
]}

机构：

[1] Tohoku Univ, Dept Chem, Grad Sch Sci, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 33期

关键词：

D O I：

10.1021/ja0617439

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The copper-catalyzed reaction between two different isocyanides produces the corresponding heteroaromatization products, imidazoles, in good yields. The reaction proceeds most probably through the activation of the sp3 C-H bond in the isocyanides by a copper catalyst, followed by a [3 + 2] cycloaddition between the cuprioisocyanide intermediates and arylisocyanides. Copyright © 2006 American Chemical Society.

引用

页码：10662 / 10663

页数：2

共 23 条

[1]

EBEL K, 1994, METHODEN ORGANISCHEN, P1

[2] Silver acetate catalysed cycloadditions of isocyanoacetates [J].

Grigg, R ;

Lansdell, MI ;

Thornton-Pett, M .

TETRAHEDRON, 1999, 55 (07) :2025-2044

[3]

Grimmett M.R., 1984, COMPREHENSIVE HETERO, V5, P345

[4]

GRIMMETT MR, 2002, SCI SYNTHESIS, V12, P325, DOI DOI 10.1055/sos-SD-012-00398

[5]

GRIMMETT MR, 1980, ADV HETEROCYCLIC CHE, V27, P241

[6] Erythro-selective aldol-type reaction of N-sulfonylaldimines with methyl isocyanoacetate catalyzed by gold(I) [J].

Hayashi, T ;

Kishi, E ;

Soloshonok, VA ;

Uozumi, Y .

TETRAHEDRON LETTERS, 1996, 37 (28) :4969-4972

[7] Synthesis of imidazole-4-carboxylic acids via solid-phase bound 3-N,N-(dimethylamino)-2-isocyanoacrylate [J].

Henkel, B .

TETRAHEDRON LETTERS, 2004, 45 (10) :2219-2221

[8] NEW PREPARATION AND SOME REACTIONS OF ORGANOCOPPER(I) ISONITRILE COMPLEXES [J].

ITO, Y ;

KONOIKE, T ;

SAEGUSA, T .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 85 (03) :395-401

[9] CATALYTIC ASYMMETRIC ALDOL REACTION - REACTION OF ALDEHYDES WITH ISOCYANOACETATE CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE-GOLD(I) COMPLEX [J].

ITO, Y ;

SAWAMURA, M ;

HAYASHI, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (20) :6405-6406

[10] INDOLE SYNTHESES WITH ORTHO-TOLYL ISOCYANIDE - 3-ACYLINDOLES AND 2-SUBSTITUTED INDOLES [J].

ITO, Y ;

KOBAYASHI, K ;

SAEGUSA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (12) :2030-2032

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