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Reactivity of Tetracyclic Iminium Salts of the Benzo[f]pyrido[2,1-a]- isoindole and Azepino[2,1-a]benzo[f]isoindole Type, with a Preliminary Analysis of their Interactions with Nucleic Acids*
-
Gerhard Maas
,
Hans-Georg Herz
Published/Copyright:
June 2, 2014
Abstract
Hydride reduction of the tetracyclic isoindolium salt derivatives 2a - c yields the neutral isoindole derivatives 9-chloro-1,2,3,4,6,6a,7,12b-octahydrobenzo[ƒ]pyrido[2,1-a]isoindole (3a), 4,4a,5,7,8,9,10,10a-octahydropyrido[2,1-a]thieno[3,2-f]isoindole (3b), and 10-chloro- 2,3,4,5,7,7a,8,13b-octahydro-1H-azepino[ƒ]pyrido[2,1-a]isoindole (3c). Oxidation of 3a with selenium dioxide is accompanied by a ring transformation and yields 8-chloro-5,5a,6,12-tetrahydrobenzo[g]pyrrolo[1,2-b]isoquinolin-12-one (4). Deprotonation of isoindolium salt derivatives 2a,c,d yields cyclic enamines which undergo ring expansion with dimethyl acetylenedicarboxylate resulting in compounds with the 4,5,6,8,8a,9-hexahydroazocino[2,1-a]benzo[ƒ]isoindole (6a), 4,6,7,9,9a,10-hexahydro-5H-azonino[2,1-a]benzo[ƒ]isoindole (6c) and 4a,5,7,8,9,10-hexahydro- 4H-azonino[2,1-a]thieno[3,2- ƒ]isoindole (6d) skeleton. Interactions of 2 with double-stranded nucleic acids are characterized by relatively large NMR upfield shifts (0.25 ppm) and signal broadening (by about 45 Hz) of aromatic ligand signals, indicating at least partial stacking with nucleobases. Rather small effects are observed, however, in melting point and viscosity increase with double strands; this is tentatively ascribed to competitive interactions with unfolded polymer parts.
Received: 2004-2-10
Published Online: 2014-6-2
Published in Print: 2004-4-1
© 1946 – 2014: Verlag der Zeitschrift für Naturforschung
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Keywords for this article
Azaheterocycles;
Iminium Salts;
Enamines;
Isoindole Derivatives;
DNA Binding
Articles in the same Issue
- Chemistry of Iminium Salts and Related Compounds
- Orthoamide, LX [1]. N,N,N’,N’-Tetraformylhydrazin – ein breit anwendbares Formylierungsmittel für aromatische Verbindungen / Orthoamide, LX [1]. N,N,N’,N’-Tetraformylhydrazine – a Formylation Agent for Aromatic Compounds of Wide Scope
- Die Synthese von 2-Methyl-5-phenacyl-1,3,4-thiadiazolen / The Synthesis of 2-Methyl-5-phenacyl-1,3,4-thiadiazoles
- Absolute Konfiguration von (+)-1,2,3,4,6,7,8,8a-Octahydro-6-isochinolon- 8a-carbonsäuremethylester und die Stereochemie einer Kupfer-katalysierten asymmetrischen Michael-Reaktion / Absolute Configuration of Methyl (+)-1,2,3,4,6,7,8,8a-Octahydro-6-isoquinolone-8a-carboxylate and Stereochemistry of a Copper-Catalyzed Asymmetric Michael Reaction
- Reactions of Quinolizine- and Pyridino[1,2–a]pyrimidine-3-diazonium Tetrafluoroborates with Aliphatic Amines
- Fries Rearrangement of Aryl Formates Promoted by BCl3. Mechanistic Evidence from 11B NMR Spectra and DFT Calculations
- C-Branched Glycals as Monosaccharidic Push-Pull Butadienes
- 1,4,5,8-Tetraazafulvalene – Darstellung schwefelhaltiger Derivate und Zuordnung des Chromophors / 1,4,5,8-Tetraazafulvalenes – Synthesis of Sulfur-Containing Derivatives and Classification of the Chromophor
- Synthesis of the Four Diastereoisomers of the N-Terminal Amino Acids of Nikkomycins via Aminoalkylation with Preformed Ternary Iminium Salts
- Reactions of 3-Chloropropeniminium Salts with Aminopyridines. Synthesis of N-Pyridylpyridinium and Pyrido[1,2-a]pyrimidinium Salts
- A New Efficient Synthesis of Substituted Luminols Using Multicomponent Reactions
- Preparation and Characterisation of N,N-Disubstituted 2-Amino-5H-selenophenes
- The Coupling-Isomerization Approach to Enimines and the First Sequential Three-Component Access to 2-Ethoxy Pyridines
- Isoxazolinium Salts in Asymmetric Synthesis. 1. Stereoselective Reduction Induced by a 3’-Alkoxy Stereocentre. A New Approach to Polyfunctionalized β-Amino Acids* [1, 2]
- Enantioselective Synthesis of Epi-Emetine Analogues: Control of the Facial Selectivity in a Three-Component Domino Knoevenagel-Hetero-Diels-Alder Reaction*
- Facile Synthesis of Novel N-Aryl-4,5,6,7-tetrahydro-benzosultams by Oxyfunctionalisation of Bicyclic Isothiazolium Salts*
- Reactivity of Tetracyclic Iminium Salts of the Benzo[f]pyrido[2,1-a]- isoindole and Azepino[2,1-a]benzo[f]isoindole Type, with a Preliminary Analysis of their Interactions with Nucleic Acids*
