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Synthesis 2020; 52(12): 1804-1822
DOI: 10.1055/s-0039-1707985
DOI: 10.1055/s-0039-1707985
paper
Straightforward Synthesis of Novel 4-Styrylquinolines/4-Styrylquinolin-2-ones and 9-Styryldihydroacridin-1(2H)-ones from Substituted 2′-Aminochalcones
A.P. would like to thank Vicerrectoría de Investigación y Extensión of the Industrial University of Santander (Grant No. 2497) for financial support.Further Information
Publication History
Received: 28 December 2019
Accepted after revision: 10 February 2020
Publication Date:
11 March 2020 (online)
Abstract
An alternative and efficient one-step approach to develop small libraries of polysubstituted 4-styrylquinolines/4-styrylquinolin-2-ones and 9-styryldihydroacridin-1-ones is described. According to this approach, new series of these compounds were straightforwardly synthesized in high yields starting from synthetically available 2′-aminochalcones and 1,3-dicarbonyl compounds in glacial acetic acid as a catalyst via the Friedländer reaction. Our approach also offers an expeditious way to access novel molecular hybrids in whose structures styryl and chalcone fragments are attached at the C4 and C3 positions, respectively, of the quinoline ring. All synthesized compounds were fully characterized by means of IR, HRMS and NMR techniques, and most were screened at the National Cancer Institute, USA, for their antitumor activity.
Key words
4-styrylquinolines - Friedländer reaction - 2′-aminochalcones - quinoline–chalcone hybrids - Claisen–Schmidt condensationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1707985.
- Supporting Information
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