Synthesis 2016; 48(24): 4519-4524
DOI: 10.1055/s-0035-1562534
paper
© Georg Thieme Verlag Stuttgart · New York

Lewis Acid Catalyzed Diels–Alder Reactions of (E)-1-Methyl-2-styrylquinolin-4(1H)-ones with ortho-Benzoquinodimethane: Synthesis of New 2-(3-Arylnaphthalen-2-yl)-1-methylquinolin-4(1H)-ones

Gustavo da Silva
Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Email: verasilva@ua.pt   Email: artur.silva@ua.pt
,
Vera L. M. Silva*
Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Email: verasilva@ua.pt   Email: artur.silva@ua.pt
,
Artur M. S. Silva*
Department of Chemistry & QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal   Email: verasilva@ua.pt   Email: artur.silva@ua.pt
› Author Affiliations
Further Information

Publication History

Received: 25 June 2016

Accepted after revision: 18 July 2016

Publication Date:
24 August 2016 (online)


Abstract

Lewis acid catalyzed cycloaddition reactions of (E)-1-methyl-2-styrylquinolin-4(1H)-ones with the very reactive diene ortho-benzoquinodimethane, generated in situ by thermal extrusion of sulfur di­oxide from 1,3-dihydrobenzo[c]thiophene 2,2-dioxide, afforded trans-2-(3-aryl-1,2,3,4-tetrahydronaphthalen-2-yl)-1-methylquinolin-4(1H)-ones in good yields. Upon DDQ-mediated dehydrogenation these adducts were converted into the corresponding 2-(3-arylnaphthalen-2-yl)-1-methylquinolin-4(1H)-ones. The influence of electron-withdrawing and electron-donating groups on the cycloaddition and dehydrogenation reactions was investigated.

Supporting Information