A CONVENIENT ENTRY TO NEW C-7-MODIFIED COLCHICINOIDS THROUGH AZIDE ALKYNE [3+2] CYCLOADDITION: APPLICATION OF RING-CONTRACTIVE REARRANGEMENTS

被引：38

作者：

Nicolaus, Norman ^{[1
]}

Reball, Jens ^{[1
]}

Sitnikov, Nikolay ^{[2
]}

Velder, Janna ^{[1
]}

Termath, Andreas ^{[1
]}

Fedorov, Alexey Yu. ^{[2
]}

Schmalz, Hans-Guenther ^{[1
]}

机构：

[1] Univ Cologne, Dept Chem, D-50939 Cologne, Germany

[2] Nizhnii Novgorod State Univ, Dept Chem, Nizhnii Novgorod 603950, Russia

来源：

HETEROCYCLES | 2011年 / 82卷 / 02期

关键词：

1,3-Dipolar Cycloaddition; 1,2,3-Triazole; Click Chemistry; Alkaloid; Antitumor Compound; Rearrangement; ANALOGS;

D O I：

10.3987/COM-10-S(E)117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reliable procedures for the preparation of azides derived from colchicine (1), allocolchicine (3) and N-acetylcolchinol (4a) were developed. These azides were then employed in Cu-catalyzed Huisgen-Sharpless [3+2] cycloaddition ("click") reactions with alkynes under microwave irradiation. The method developed opens a convenient and efficient access to libraries of new C-7-modified colchicinoids (triazole derivatives). In addition, a plausible mechanistic rationale for the colchicine-allocolchicine rearrangement is suggested.

引用

页码：1585 / +

页数：17

共 29 条

[1] Metal catalyzed diazo transfer for the synthesis of azides from amines [J].