NMR spectroscopic properties of furo[2′,3′:4,5]pyrrolo[1,2-d][1,2,4]triazine derivatives

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Abstract

The 1H and 13C NMR spectroscopic properties of a series of furo[2′,3′:4,5]pyrrolo[1,2-d][1,2,4]triazin-8(7H)-ones and -thiones were investigated. The influence of various electron donating as well as electron withdrawing substituents at C-5 or N-7 on 1H NMR chemical shifts as well as 13C chemical shifts at C8 were observed. The 5-chloromethyl group had a little influence on the chemical shift of H-7 proton and the 8-thione group causes deshielding of H-7 as well as H-5 protons in comparison with the C-8 carbonyl group.

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  • Astakhina V Voievudskyi M Kharchenko O Novikov V Komarovska-Porohnyavets E Petukhova O (2016) Synthesis and biological activity of novel ethyl esthers of 4-R-68-dimethyl-1-oxo-12-dihydropyrrolo[12-d]triazine-7-carboxylic acids. J. Heterocycl. Chem. 53: 421-428.

  • Beccalli EM Broggini G Martinelli M Sottocornola S (2008) Microwave-assisted intramolecular cyclistion of electron-rich heterocycle derivatives by a palladium-catalyzed coupling reaction. Synthesis 2008: 136-140.

  • El-Gendy AA Said MM Ghareb N Mostafa YM El-Ashry ESH (2008) Synthesis and biological activity of functionalized indole -2-carboxylates triazino- and pyridazino-indoles. Arch. Pharm. 341: 294-300.

  • George DM Breinlinger EC Friedman M Zhang Y Wang J Argiriadi M Bansal-Pakala P Barth M Duignan DB Honore P Lang Q Mittelstadt S Potin D Rundell L Edmunds JJ (2015) Discovery of selective and orally bioavailable protein kinase Cθ (PKCθ) inhibitors from a fragment hit. J. Med. Chem. 58: 222-236.

  • Lauria A Alfio A Bonsignore R Gentile C Martorana A Gennaro G Barone G Terenzi A Almerico AM (2014) New benzothieno[32-d]-123-triazines with antiproliferative activity: Synthesis spectroscopic studies and biological activity. Bioorg. Med. Chem. Lett. 24: 3291–3297.

  • Khutova BM Klyuchko SV Gurenko AO Vasilenko AN Balya AG Rusanov EB Brovarets VS (2012) Conversions of 7-aryl-7H-pyrazolo[34-d]-[123]triazin-4-ols by the action of phosphorus pentoxide pentasulfide and oxychloride. Chem. Heterocycl. Comp. 48: 1251-1262.

  • Krutošíková A Dandárová M Chylová J Vegh D (1992) Condensed O- N-heterocycles by the transformation of azidoacrylates. Monatsh. Chem. 123: 807-815.

  • Fehér D Barlow R McAtee J Hemscheidt TK (2010) Highly Brominated Antimicrobial Metabolites from a Marine Pseudoalteromonas sp. J. Nat. Prod. 73: 1963–1966.

  • Sparey T Abeywickrema P Almond S Brandon N Byrne N Campbell A Hutson PH Jacobson M Jones B Munshi S Pascarella D Pike A Prasad G S Sachs N Sakatis M Sardana V Venkatraman S Young MB (2008) The discovery of fused pyrrole carboxylic acid as novel potent D-aminoacid oxidase (DAO) inhibitors. Bioorg. Med. Chem. Lett. 18: 3386-3391.

  • Umezawa K Nakamura Y Makino H Citterio D Suzuki K (2008) Fluorescent dyes in the visible-near-infrar region. J. Am. Chem. Soc. 130: 1550-1551.

  • Zemanová I Gašparová R Kraic F Kružlicová D Maliar T Boháč A Addová G (2017) Synthesis of furo[2'3':45]pyrrolo[12-d][124]triazine derivatives and their antibacterial activity. Arkivoc part iv: 184-193.

  • Zhao H Koenig SG Dankwardt JW Singh SP (2014) Practical nonazide synthesis of D-amino acid oxidase inhibitor via sequential Erlenmeyer-Plochl reaction and ligand-free copper (I) amination protocol. Org. Process Res. Dev. 18: 198-204.

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