Steric inhibition to cyclization of β-keto amides to indeno[1,2,3-de]quinolinones and related compounds

B. Staskun*

*Corresponding author for this work

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The preferred conformation of N-ethyl-2,2,2′-trichlorobenzoylacetanilide (1f) was deduced from 1H NMR data and served to account for the failure of 1f to cyclize in H2SO4 in terms of a steric hindrance to attainment of the requisite conformation for ring closure. Consistent with this view was the observation that pentachlorodihydroquinolinone 7a with H2SO4 underwent ring opening to give as chief product alkene 8, and only a minor amount of indenoquinolinone 2. Substrate 7a was formed, in preference to amide 11, from difluorooxyborane 6a and SO2Cl2, on allowing HCl to escape from the reaction mixture.

Original languageEnglish
Pages (from-to)2482-2485
Number of pages4
JournalJournal of Organic Chemistry
Volume45
Issue number12
Publication statusPublished - 1980

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