Reexamination of some reactions of 3-(D-galactosylidenehydrazino)-1,2,4-triazino[5,6-b]indole. 2003

M A E Shaban, and A Z Nasr, and A E A Morgaan
Department of Chemistry, Faculty of Science, Alexandria University, Ibrahimia, Alexandria, Egypt. mae_shaban@hotmail.com

Incorrect structures described in the literature for the products of reactions of the title compound 6 were reexamined and corrected. Thus, the product of acetylation of 6 with acetic anhydride in the presence of pyridine was found to be the mono-N-penta-O-acetyl derivative 10 and not the previously described di-N-penta-O-acetyl derivative 7. Assignment of structure 10 was based on 1H NMR data as well as its ability to undergo oxidative cyclization with Br2/AcOH to give 12. The previously assigned structure 7 would be incapable of undergoing such cyclization. The linear structure 12 rather than the angular regioisomer 3c was assigned on the basis of its UV absorption pattern and 1H NMR NOE spectra. Attempted preparation of 7 by increasing the duration of the reaction gave only compound 10. A di-N-acetyl-penta-O-acetyl derivative, however, was obtained with acetyl bromide in the presence of pyridine to which structure 8 rather than structure 7 or 9 was assigned on the basis of 1H NMR NOE studies. Acetylation of the triazolo-triazino-indole 11 gave a product identical to 12; structure 15 previously assigned to this product is, therefore, in error. Finally, the angular annelated structure 3e previously ascribed to the oxidative cyclization product of the 5-methylhydrazone congener of 6 (13) is now rectified to the linear annelated structure 14; the latter was found to be identical to the product obtained by N-methylation of the unequivocally linear 1,2,4-triazolo[4,3-b]1,2,4-triazino[5,6-b]indole 11. Compound 8 was found to exist in the preponderantly populated sickle (bent) conformation 18 in contrast to compounds 10 and 12 which were found to adopt the extended planar zigzag conformations 19 and 20 respectively.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D007211 Indoles Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D003500 Cyclization Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Cyclizations
D013055 Spectrophotometry, Infrared Spectrophotometry in the infrared region, usually for the purpose of chemical analysis through measurement of absorption spectra associated with rotational and vibrational energy levels of molecules. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) IR Spectra,Infrared Spectrophotometry,IR Spectras,Spectra, IR
D013056 Spectrophotometry, Ultraviolet Determination of the spectra of ultraviolet absorption by specific molecules in gases or liquids, for example Cl2, SO2, NO2, CS2, ozone, mercury vapor, and various unsaturated compounds. (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed) Ultraviolet Spectrophotometry
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D014227 Triazines Heterocyclic rings containing three nitrogen atoms, commonly in 1,2,4 or 1,3,5 or 2,4,6 formats. Some are used as HERBICIDES. Triazine,Benzotriazines

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