Chemistry Section, Laboratory of Comparative Carcinogenesis, National Cancer Institute at Frederick, Frederick, Maryland 21702, USA.
Org Lett. 2010 Oct 1;12(19):4256-9. doi: 10.1021/ol101645k.
The use of Cu(I)-catalyzed "click" reactions of alkyne-substituted diazeniumdiolate prodrugs with bis- and tetrakis-azido compounds is described. The "click" reaction for the bis-azide using CuSO(4)/Na-ascorbate predominantly gave the expected bis-triazole. However, CuI/diisopropylethylamine predominantly gave uncommon triazolo-triazole products as a result of oxidative coupling. Neither set of "click" conditions showed evidence of compromising the integrity of the diazeniumdiolate groups. The chemistry developed has applications in the synthesis of polyvalent and dendritic nitric oxide donors.
本文描述了炔基取代的重氮二氧戊环前药与双叠氮和四叠氮化合物的 Cu(I)催化“点击”反应的应用。使用 CuSO(4)/Na-抗坏血酸的双叠氮“点击”反应主要生成预期的双三唑。然而,CuI/二异丙基乙胺主要由于氧化偶联生成不常见的三唑并三唑产物。这两组“点击”条件都没有显示出破坏重氮二氧戊环基团完整性的证据。所开发的化学具有在多价和树枝状一氧化氮供体合成中的应用。