Concise and Versatile Multicomponent Synthesis of Multisubstituted Polyfunctional Dihydropyrroles

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• 作者：Qiuhua Zhu ; Huanfeng Jiang ; Jinghao Li ; Shuwen Liu ; Chenglai Xia ; Min Zhang
• 刊名：Journal of Combinatorial Chemistry
• 出版年：2009
• 出版时间：July 13, 2009
• 年：2009
• 卷：11
• 期：4
• 页码：685-696
• 全文大小：279K
• 年卷期：v.11,no.4(July 13, 2009)
• ISSN：1520-4774

文摘

Tetra- and pentasubstituted polyfunctional dihydropyrroles have been concisely synthesized in high yields by two different processes of the one-pot multicomponent reactions (MCRs) of but-2-ynedioates 1, amines 2, and aldehydes 3 at room temperature or at 70 °C. The first one involves a domino hydroamination/nucleophilic addition/amidation-cyclization process and leads to the formation of tetrasubstituted polyfunctional dihydropyrroles 4. The second undergoes hydroamination/amidation/intramolecular cyclization/imine-enamine tautomerization sequence and results in pentasubstituted products 5. The structures of 4 and 5 were confirmed by single-crystal X-ray diffraction. These novel methodologies provide easy access to diversely multisubstituted polyfunctional dihydropyrrole libraries. The primary biological screening in vitro against HIV-1 has shown that 22 tested compounds have exhibited significant activity with IC₅₀ in micromolar range (38−58 μM).