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

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 trans...

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Autores principales: Khodjaniyazov, Khamid U., Makhmudov, Utkir S., Turgunov, Kambarali K., Elmuradov, Burkhon Z.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
Materias:
Research Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5730303/
https://www.ncbi.nlm.nih.gov/pubmed/29250366
http://dx.doi.org/10.1107/S2056989017013093
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author Khodjaniyazov, Khamid U.
Makhmudov, Utkir S.
Turgunov, Kambarali K.
Elmuradov, Burkhon Z.
author_facet Khodjaniyazov, Khamid U.
Makhmudov, Utkir S.
Turgunov, Kambarali K.
Elmuradov, Burkhon Z.
author_sort Khodjaniyazov, Khamid U.
collection PubMed
description 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, 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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spelling pubmed-57303032017-12-15 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 Khodjaniyazov, Khamid U. Makhmudov, Utkir S. Turgunov, Kambarali K. Elmuradov, Burkhon Z. Acta Crystallogr E Crystallogr Commun Research Communications 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, 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. International Union of Crystallography 2017-09-19 /pmc/articles/PMC5730303/ /pubmed/29250366 http://dx.doi.org/10.1107/S2056989017013093 Text en © Khodjaniyazov et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Khodjaniyazov, Khamid U.
Makhmudov, Utkir S.
Turgunov, Kambarali K.
Elmuradov, Burkhon Z.
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5730303/
https://www.ncbi.nlm.nih.gov/pubmed/29250366
http://dx.doi.org/10.1107/S2056989017013093
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