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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
-
Christiane Kühn
,
U.-W. Grummt
Published/Copyright:
June 2, 2014
Abstract
In order to obtain sulfur-containing tetraazafulvalenes the derivatives 1 - 3 were cross-coupled with different types of acetylenes via palladium-catalyzed reactions. Starting from the tetrabromoaryl derivative 3a, four bromine atoms could be replaced by 2-ethynylthiophene. Under analogous conditions, the methylsulfanyl esters 7 -11 could be obtained by employing 4-ethynylbenzoic acid 4-(methylsulfanyl)butylester 6. Lipoic acid could be integrated into tetraazafulvalenes successfully in a two step reaction. First, the Sonogashira coupling method yielded the compound 12 possessing two (4-anilino)ethynyl residues which were then condensed with lipoic acid to give derivative 13.
Whereas the NMR data suggest the predominance of prototropic form A, UV/vis spectra of the deeply colored tetraazafulvalenes are in favor with structure B rather than with structure A. DFT calculations at the B3LYP/6-31G(d) level showed that tautomeric form B is about 60 kJ/mol more stable than A. In addition, time-dependent density functional theory calculations support the substructure of two crossed diazaheptamethinemerocyanines.
Received: 2004-1-9
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
Tetraazafulvalenes;
Cross-Coupling Reactions;
Lipoic Acid;
Chromophoric System
Articles in the same Issue
- Chemistry of Iminium Salts and Related Compounds
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- 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
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- 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*
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