- Iodine-Promoted Formal [5+1] Annulation of 2-Vinylanilines and Thiurams: A Facile Approach to the Synthesis of 2-Aminoquinolines
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Quinolines, especially 2-aminoquinolines, are highly important heterocycles in medicinal chemistry. 2-Aminoquinolines can be synthesized by stepwise construction of the quinoline ring followed by additional amination; however, this protocol is cumbersome. Here, we describe a [5+1]-cyclization of 2-vinylanilines with tetraalkylthiuram disulfides in the presence of iodine and copper(II) triflate. This reaction directly employs readily available and low-cost thiuram as both a C1 synthon and a nitrogen source, providing a facile approach to one-step syntheses of a variety of 2-aminoquinolines in good to excellent yields.
- Jiao, Jing,Wang, Pengyang,Xiao, Fangtao,Zhang, Zhipeng
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- Auto-tandem catalysis: Synthesis of acridines by Pd-catalyzed C=C bond formation and C(sp2)-N cross-coupling
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A facile palladium-catalyzed synthesis of acridines has been realized by consecutive C=C double bond formation and C-N cross-coupling. A variety of functionalized acridines can be accessed from easily available o-dihalobenzenes and N-tosylhydrazones in a single operation. This one-pot protocol has a wide scope with respect to both coupling partners, and provides an efficient route to functionalized acridine derivatives, which are generally difficult to synthesize by previously known methods.
- Huang, Zhongxing,Yang, Yang,Xiao, Qing,Zhang, Yan,Wang, Jianbo
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p. 6586 - 6593
(2013/01/15)
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