Selective C-formylation of 8,9,10,11-tetrahydropyrido[20,30:4,5]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.
CITATION STYLE
Khodjaniyazov, K. U., Makhmudov, U. S., Turgunov, K. K., & Elmuradov, B. Z. (2017). 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, 73(10), 1497–1500. https://doi.org/10.1107/S2056989017013093
Mendeley helps you to discover research relevant for your work.