The mechanism of indeno[1,2,3-de]quinolin-2-one formation

Peter C. Meltzer, Benjamin Staskun*

*Corresponding author for this work

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Abstract

The unambiguous synthesis of 1,6-dichloro-3-ethylindeno[1,2,3-de]quinolin-2(3H)-one (7) was undertaken. Product 7 was found to be identical with that derived by sulfuric acid catalyzed cyclization of 2,2,4′-trichloro-N-ethylbenzoylacetanilide (4). This is evidence that 7 arises from 4 via a "direct" cyclization intermediate. A convenient modification of the Cook and Koelsch indenoquinolinone synthesis, which afforded 7 by a shorter route, is reported. The diagnostically useful anisotropic deshielding of the C-7 and C-10 protons by the halogen at C-1 and C-6 in the 1H NMR spectrum of 7 is described.

Original languageEnglish
Pages (from-to)2977-2980
Number of pages4
JournalJournal of Organic Chemistry
Volume42
Issue number18
Publication statusPublished - 1977

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Meltzer, P. C., & Staskun, B. (1977). The mechanism of indeno[1,2,3-de]quinolin-2-one formation. Journal of Organic Chemistry, 42(18), 2977-2980.