An unusual reaction of 2-(2-pyridylcarbonyl)- and 2-(2-quinolylcarbonyl)benzoyl chlorides with <i>p</i>-nitroaniline

Abstract

In the reaction of 2-(2-pyridylcarbonyl)benzoyl chloride, which exists in the form of 6,11-dioxo-6,11dihydrobenzo[b]quinolizinium chloride, with p-nitroaniline, 2-(4-nitrophenylimino)-6,11-dihydro-2H-benzo-[b]quinolizine-6,11-dione is unexpectedly formed. When it reacts with water or methanol there is an opening of the quinolizine ring and aromatization of the quinoid fragment with the formation of 2-[4-(4-nitrophenylamino)-2-pyridylcarbonyl]benzoic acid or its methyl ester. Under the action of antimony pentachloride, 2-(2-quinolylcarbonyl)benzoylchloride-3-(2-quinolyl)-3-chloro-1,3-dihydrobenzo[c]furan-1-one is converted to 3-(2-quinolyl)-1,3-dihydrobenzo[c]furan-1-on-3-ylium hexachlorantimonate, which undergoes isomerizing recyclization upon heating to 7,12-dioxo-7,12-dihydrobenzo[b]hexachloroantimonate. The latter enters into an analogous reaction with p-nitroaniline, thereby forming 5-(4-nitrophenylimino)-7,12-dihydro-5H-dibenzo[b,f]quinolizine-7,2-dione.

How to Cite
Karlivan, G. A.; Valter, R. É.; Batse, A. É.; Petrova, M. V.; Kampare, R. B. Chem. Heterocycl. Compd. 1995, 31, 817. [Khim. Geterotsikl. Soedin. 1995, 938.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01170742