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Synlett 2022; 33(06): 569-574
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

Jing Jiao‡
,
Pengyang Wang‡
,
Fangtao Xiao
,
Zhipeng Zhang  ∗
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).
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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.

Key words

vinylanilines - thiuram - cyclization - iodine - aminoquinolines - copper catalysis

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

© 2022. Thieme. All rights reserved

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