Unusual formation of (<i>E</i>)-11-(aminomethylene)-8,9,10,11-tetrahydropyrido[2′,3′:4,5]pyrimido[1,2-<i>a</i>]azepin-5(7<i>H</i>)-one and its crystal structure
Khamid U. KhodjaniyazovS.Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences of, Uzbekistan Mirzo Ulugbek Str., 77, Tashkent 100170, UzbekistanUtkir S. MakhmudovS.Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences of, Uzbekistan Mirzo Ulugbek Str., 77, Tashkent 100170, UzbekistanK. K. TurgunovS.Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences of, Uzbekistan Mirzo Ulugbek Str., 77, Tashkent 100170, UzbekistanBurkhon ElmuradovS.Yunusov Institute of the Chemistry of Plant Substances Academy of Sciences of, Uzbekistan Mirzo Ulugbek Str., 77, Tashkent 100170, Uzbekistan
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Selective C-formylation of 8,9,10,11-tetrahydropyrido[2′,3′:4,5]pyrimido[1,2- a ]-azepin-5(7 H )-one has been studied for the first time. It was revealed that formylation proceeds by the formation of an intermediate salt, which due to the re-amination process on treatment with aqueous ammonia transformed into the corresponding ( E )-11-(aminomethylene)-8,9,10,11-tetrahydropyrido[2′,3′:4,5]-pyrimido[1,2- a ]azepin-5(7 H )-one, C 13 H 14 N 4 O, as an E -isomer. Formylation 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 molecule, the seven-membered pentamethylene ring adopts a twist-boat conformation.
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