Journal
SYNTHESIS-STUTTGART
Volume 48, Issue 24, Pages 4519-4524Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0035-1562534
Keywords
quinolin-4(1H)-ones; ortho-benzoquinodimethane; cyclo-additions; Diels-Alder reaction; dehydrogenation; NMR spectroscopy
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Funding
- University of Aveiro
- 'Fundacao para a Ciencia e Tecnologia' (FCT/MEC, Portugal) [FCT UID/QUI/00062/2013]
- FEDER
- FCT/MCTES [SFRH/BPD/108807/2015]
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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-2yl)-1-methylquinolin-4(1H)-ones. The influence of electron-withdrawing and electron-donating groups on the cycloaddition and dehydrogenation reactions was investigated.
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