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Synlett 2022; 33(06): 569-574
DOI: 10.1055/a-1735-6250
DOI: 10.1055/a-1735-6250
letter
Iodine-Promoted Formal [5+1] Annulation of 2-Vinylanilines and Thiurams: A Facile Approach to the Synthesis of 2-Aminoquinolines
This work was supported by the National Natural Science Foundation of China (21702059), Shanghai Pujiang Program (18PJ1402200), and Fundamental Research Funds for the Central Universities (222201814014, JKVJ1211010, JKVJ12001010).
Abstract
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1735-6250.
- Supporting Information
Publication History
Received: 15 December 2021
Accepted after revision: 11 January 2022
Accepted Manuscript online:
11 January 2022
Article published online:
07 February 2022
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