“Click” Reaction in Conjunction with Diazeniumdiolate Chemistry: Developing High-Load Nitric Oxide Donors

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• 作者：Oyebola A. Oladeinde ; Sam Y. Hong ; Ryan J. Holland ; Anna E. Maciag ; Larry K. Keefer ; Joseph E. Saavedra ; Rahul S. Nandurdikar
• 刊名：Organic Letters
• 出版年：2010
• 出版时间：October 1, 2010
• 年：2010
• 卷：12
• 期：19
• 页码：4256-4259
• 全文大小：212K
• 年卷期：v.12,no.19(October 1, 2010)
• ISSN：1523-7052

文摘

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 CuSO₄/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.