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Original Articles

CONDENSATION OF o-PHENYLENEDIAMINE WITH α-DIKETONES. PREPARATION AND PHOSPHORYLATION OF NEW α-DIKETONE MONOANILS

Pages 341-349 | Received 04 Oct 1990, Accepted 22 Jan 1991, Published online: 23 Sep 2006
 

Abstract

Condensation of o-phenylenediamine 5 with N-methylisatine 4b and with benzocoumaranedione 12 under different conditions was studied. Monoanils N-methyl-3-(2-aminophenylimino)-indoline-2-one 6b and benzocoumaran-3-(2-aminophenylimino)-2-one 13 were isolated. Dimethyl phosphite add to anils 6b and/or 13 to give the corresponding quinoxalines 7 and 14 respectively. On the other hand, diethyl phosphite add to carbonyl-oxygen double bond in compounds 6b & 13 to give the respective phosphate adducts 16 & 17a. Structural reasonings are based on chemical and spectroscopic results.

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