Unusual formation of ()-11-(amino-methyl-ene)-8,9,10,11-tetra-hydro-pyrido[2',3':4,5]pyrimido[1,2-]azepin-5(7)-one and its crystal structure.

Authors:
Kambarali K Turgunov
Kambarali K Turgunov
S. Yunusov Institute of the Chemistry of Plant Substances
Burkhon Z Elmuradov
Burkhon Z Elmuradov
S.Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences of

Acta Crystallogr E Crystallogr Commun 2017 Oct 19;73(Pt 10):1497-1500. Epub 2017 Sep 19.

S.Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences of, Uzbekistan Mirzo Ulugbek Str., 77, Tashkent 100170, Uzbekistan.

Selective C-formyl-ation of 8,9,10,11-tetra-hydro-pyrido[2',3':4,5]pyrimido[1,2-]-azepin-5(7)-one has been studied for the first time. It was revealed that formyl-ation proceeds by the formation of an inter-mediate salt, which due to the re-amination process on treatment with aqueous ammonia transformed into the corresponding ()-11-(amino-methyl-ene)-8,9,10,11-tetra-hydro-pyrido[2',3':4,5]-pyrimido[1,2-]azepin-5(7)-one, CHNO, as an -isomer. Formyl-ation was carried out by Vilsmeier-Haack reagent and the structure of the synthesized compound was confirmed by X-ray structural analysis, spectroscopic and LC-MS methods. In the mol-ecule, the seven-membered penta-methyl-ene ring adopts a twist-boat conformation.

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http://dx.doi.org/10.1107/S2056989017013093DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5730303PMC

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October 2017
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