A CONVENIENT ENTRY TO NEW C-7-MODIFIED COLCHICINOIDS THROUGH AZIDE ALKYNE [3+2] CYCLOADDITION: APPLICATION OF RING-CONTRACTIVE REARRANGEMENTS
A CONVENIENT ENTRY TO NEW C-7-MODIFIED COLCHICINOIDS THROUGH AZIDE ALKYNE [3+2] CYCLOADDITION: APPLICATION OF RING-CONTRACTIVE REARRANGEMENTS
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DOI：
10.3987/com-10-s(e)117
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发表时间：
2011-03-01
期刊：
影响因子：
0.6
通讯作者：
Schmalz, Hans-Guenther
中科院分区：
文献类型：
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作者：
Nicolaus, Norman;Reball, Jens;Schmalz, Hans-Guenther
建立了由秋水仙碱(1)、异基因秋水仙碱(3)和N-乙酰秋水仙醇(4a)衍生的叠氮化物的可靠制备方法。然后，这些叠氮化合物被用于铜催化的惠斯根-夏普莱斯[3+2]环加成(“点击”)反应与炔烃在微波辐射下。所开发的方法为新的C-7修饰的秋水仙素(三氮唑衍生物)的文库提供了一个方便和有效的途径。此外，还提出了秋水仙碱-异种秋水仙碱重排的合理的机理。
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.