Journal
ORGANIC LETTERS
Volume 5, Issue 13, Pages 2251-2253Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol034559q
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Nitration of 3-bromobenzaldehyde followed by sodium dithionite reduction provides 5-bromo-2-aminobenzaldehyde, which undergoes the Friedlander condensation with a variety of enolizable ketones to afford bidentate and tridentate 6-bromoquinoline derivatives. These species may be dimerized with Ni(0) to form biquinolines or treated under Sonogashira conditions to afford 6-alkynyl derivatives. Examination of optical properties indicate an unusually high emission quantum yield for 6,6'-biquinolines.
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