Novel intramolecular two-substituent migration accompanying indenoquinolone formation

B. Staskun*

*Corresponding author for this work

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Treatment of 2,2,4′-trichloro-2′,5′-dimethylbenzoylacetanilide (2c) with H2SO4 gave 1,5-dichloro-4,6-dimethylindeno[1,2,3-de]quinolin-2(3H)-one (3a) which was identified by spectral (IR) comparison with various isomeric 3. Product 3a may arise via concerted, intramolecular 1,2-shifts of two substituents during cyclization. Substrate 2,2,2′,4′-tetrachloro-3′,5′-dimethylbenzoylacetanilide (2e), in which this rearrangement is not feasible, was converted into 1,4,6-trichloro-5-methyl-7H-dibenz[f, ij]isoquinolin-2(3H)-one (5b).

Original languageEnglish
Pages (from-to)5069-5079
Number of pages11
JournalTetrahedron
Volume28
Issue number19
DOIs
Publication statusPublished - 1972

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