Ipso substitution as a route to benzo[c]quinolizines and 4-hydroxycoumarins

Yannan Liu, Mark J. Kurth

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

A convenient ipso substitution method for the preparation of benzo [c] quinolizine (2) and 4-hydroxy-3-(2′-pyridyl)coumarin (3) has been developed. The intramolecular nucleophilic substitution reaction of 3-oxo-2-(2′-pyridyl)-(2-halophenyl)propanoate (1) in refluxing xylenes gives initially benzo[c]-quinolizine, while further heating results in the formation of 4-hydroxycoumarin. A mechanism has been proposed to rationalize the two competitive reaction pathways, and the role of HCl is discussed. Under optimized conditions, seven benzo [c] quinolizines and five coumarins were prepared in moderate to good yields.

Original languageEnglish (US)
Pages (from-to)2082-2086
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number7
DOIs
StatePublished - Apr 5 2002

ASJC Scopus subject areas

  • Organic Chemistry

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