Synthesis 2020; 52(12): 1804-1822
DOI: 10.1055/s-0039-1707985
paper
© Georg Thieme Verlag Stuttgart · New York

Straightforward Synthesis of Novel 4-Styrylquinolines/4-Styrylquinolin-2-ones and 9-Styryldihydroacridin-1(2H)-ones from Substituted 2′-Aminochalcones

Angie Meléndez
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia   Email: apalma@uis.edu.co
,
Esteban Plata
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia   Email: apalma@uis.edu.co
,
Diego Rodríguez
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia   Email: apalma@uis.edu.co
,
Diana Ardila
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia   Email: apalma@uis.edu.co
,
Sergio A. Guerrero
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia   Email: apalma@uis.edu.co
,
Lina M. Acosta
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia   Email: apalma@uis.edu.co
,
Justo Cobo
b   Inorganic and Organic Department, University of Jaén, Campus Las Lagunillas s/n, 23071 Jaén, Spain
,
Manuel Nogueras
b   Inorganic and Organic Department, University of Jaén, Campus Las Lagunillas s/n, 23071 Jaén, Spain
,
Alirio Palma
a   Laboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia   Email: apalma@uis.edu.co
› Author Affiliations
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.

Supporting Information

 
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