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Paper | Regular issue | Vol 71, No. 1, 2007, pp.13-18
Published online, 7th November, 2006
DOI: 10.3987/COM-06-10854
Unconventional Recyclization of Cotarnine under the Action of 1,3-Dimethylbarbituric Acid

Konstantin A. Krasnov, Viktor G. Kartsev,* and Viktor N. Khrustalev

*InterBioScreen Ltd., Chernogolovka, Moscow, Russia

Abstract

The result of condensation of cotarnine with 1,3-dimethylbarbituric acid depends essentially on the temperature. In a harsh conditions (190 °C, without solvent), an unconventional tandem rearrangement proceeds to give (5aR*,9aS*)-11-methoxy-6,8-dimethyl-7,9-dioxo-5,6,7,8,9,10-hexahydro-5a-H-1,3-dioxa-6,8-diaza-cyclopenta[b]anthracene-9a-carboxylic acid methylamide. The structure of this compound was confirmed by XRD. The rearrangement proceeding via the [1,5] H-shift is similar to T-reactions.