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

Angie Meléndez; Esteban Plata; Diego Rodríguez; Diana Ardila; Sergio A. Guerrero; Lina M. Acosta; Justo Cobo; Manuel Nogueras; Alirio Palma

doi:10.1055/s-0039-1707985

Synthesis, Table of Contents

Synthesis 2020; 52(12): 1804-1822
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

Angie Meléndez

^aLaboratorio 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

^aLaboratorio 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

^aLaboratorio 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

^aLaboratorio 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

^aLaboratorio 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

^aLaboratorio 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

^bInorganic and Organic Department, University of Jaén, Campus Las Lagunillas s/n, 23071 Jaén, Spain

,

Manuel Nogueras

^bInorganic and Organic Department, University of Jaén, Campus Las Lagunillas s/n, 23071 Jaén, Spain

,

Alirio Palma∗

^aLaboratorio 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

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Abstract

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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 condensation

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References

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