A Copper-Catalyzed Tandem Cyclization Reaction of Aminoalkynes with Alkynes for the Construction of Tetrahydropyrrolo[1,2-a]quinolines Scaffold. | LitMetric
Zhejiang Province Key Laboratory of Anti-Cancer Drug Research, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, 310058, China.
Published: November 2017
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Article Abstract
A synthetic method for diversely substituted tetrahydropyrrolo[1,2-a]quinolines was developed via CuCl-catalyzed cascade transformation of internal aminoalkynes with alkynes under microwave- irradiation.
Key Laboratory of Plant Resources Conservation and Sustainable Utilization, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences Guangzhou 510650 China +86-0531-89631227.
Putrescine is a toxic biogenic amine produced in the process of food spoilage, and a high concentration of biogenic amines in foods will cause health problems such as abnormal blood pressure, headaches and tachycardia asthma/worsening asthma. The detection of putrescine is necessary. However, traditional putrescine detection requires specialized instruments and complex operations.
Dewar benzenes, the metastable valence isomers of benzenes, have been extensively studied both experimentally and theoretically. In contrast, little is known about Dewar metallabenzenes having a transition metal in the skeletal framework, despite the recent intensive interest in the development of chemistry of metallabenzenes. Herein, we report the isolation and characterization of the first examples of structurally characterized Dewar metallabenzenes.
Herein, we report a protocol for PtI-catalyzed three-component cascade cycloaddition reactions between γ-aminoalkynes and electron-deficient alkynes to afford highly substituted cyclohexadiene--pyrrolidines in good yields. On the basis of the results of the control experiments and density functional theory calculations, we present a plausible mechanism that proceeds via two key intermediates. The overall transformation involves the cleavage and formation of multiple C-C and C-N bonds and a previously unreported reaction mode of a seven-membered nitrogen heterocyclic intermediate.
An iron catalyst has been developed for the transfer hydrogenation of carbon-carbon multiple bonds. Using a well-defined β-diketiminate iron(II) precatalyst, a sacrificial amine and a borane, even simple, unactivated alkenes such as 1-hexene undergo hydrogenation within 1 h at room temperature. Tuning the reagent stoichiometry allows for semi- and complete hydrogenation of terminal alkynes.
A synthetic method for diversely substituted tetrahydropyrrolo[1,2-a]quinolines was developed via CuCl-catalyzed cascade transformation of internal aminoalkynes with alkynes under microwave- irradiation.
