Unusual formation of (E)-11-(aminomethylene)-8,9,10,11-tetrahydropyrido[2′,3′:4,5]pyrimido[1,2-a]azepin-5(7H)-one and its crystal structure

Acta Crystallographica Section E: Crystallographic Communications

卷:73

Khamid U. Khodjaniyazov¹  Kambarali K. Turgunov¹  Utkir S. Makhmudov¹  Burkhon Z. Elmuradov¹ 

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

关键词: fused pyrimidines;    formylation;    Vilsmeier–Haack reagent;    X-ray structure analysis;    crystal structure;   

DOI  :  10.1107/S2056989017013093

来源: DOAJ

【 摘 要 】

Selective C-formylation of 8,9,10,11-tetrahydropyrido[2′,3′:4,5]pyrimido[1,2-a]-azepin-5(7H)-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(7H)-one, C13H14N4O, 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.

【 授权许可】

Unknown