By reaction of heterocyclic-substituted 1-azo-naphth-2-ols with the Vilsmeier reagent or with strong acids polycyclic azolo[1,2,4]triazinium salts are formed in good yields. The azolo[1,2,4] triazinium salts exhibit similar UV=Vis absorption properties as the starting azo compounds, but in contrast to those the fluorescence appears in the visible range.
Graphical Abstract
![Formation of Azolo[1,2,4]triazinium Salts by Reaction of Heterocyclicsubstituted 1-Azo-naphthalen-2-ols with Strong Acids](/document/doi/10.5560/znb.2014-4001/asset/graphic/s69b0501.png)
Formation of Azolo[1,2,4]triazinium Salts by Reaction of Heterocyclicsubstituted 1-Azo-naphthalen-2-ols with Strong Acids
Keywords: 1-Arylazo-2-naphthols; Benzo[b]naphtho[2,1-e]thiazolo[2,3-c][1,2,4]triazinium Salts; Naphtho[2,1-e]thiazolo[2,3-c][1,2,4]triazinium Salts; Naphtho[2,1-e][1,3,4]thiadiazolo [2,3-c][1,3,4]triazinium Salts; Vilsmeier Reaction
Received: 2014-1-2
Published Online: 2014-6-2
Published in Print: 2014-5-1
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Artikel in diesem Heft
- Chemistry of Iminium Salts, Imines, and Related Compounds
- Thiaminpyrophosphat – ein natürlich vorkommendes Iminium-Salz. Seine Bedeutung für die mikrobiellen Prozesse bei der Weinbereitung und die Aromabildung im Wein / Thiamine Diphosphate – A Natural Iminium Salt. Its Role in Microbiological Processes During Wine Preparation and on the Aroma of Wine
- Formation of Azolo[1,2,4]triazinium Salts by Reaction of Heterocyclicsubstituted 1-Azo-naphthalen-2-ols with Strong Acids
- Synthesis of Methyl 3-Azidothieno[2,3-b]pyridine-2-carboxylates and Application of the Huisgen Reaction
- Orthoamide und Iminiumsalze, LXXXVII [1]. Eine neue, einfache Synthese für 1,3-Dimethylthymin / Orthoamides and Iminium Salts LXXXVII [1]. A New and Facile Synthesis of 1,3-Dimethylthymine
- Orthoamide und Iminiumsalze, LXXXIV [1]. Die Synthese von starken Formylierungsmitteln im präparativen Großmaßstab: Tris(dichlormethyl)amin / Orthoamides and Iminiumsalts LXXXIV [1]. The Synthesis of Strong Formylating Reagents on a Large Preparative Scale: Tris(chloromethyl)amine
- Orthoamide und Iminiumsalze, LXXXV [1]. Die Synthese von starken Formylierungsmitteln im präparativen Großmaßstab: N,N,N',N'- Tetraformylhydrazin und Formyl-aalen [Tris(diformylamino)methan] / Orthoamides and Iminium Salts LXXXV [1]. The Synthesis of Strong Formylating Reagents on a Large Preparative Scale: N;N;N';N'-Tetraformylhydrazine and Formyl-aalen [Tris(diformylamino)methane]
- Phenothiazine-Aromatic Hydrocarbon Acceptor Dyads as Photo-induced Electron Transfer Systems by Ugi Four-Component Reaction
- A Simple Metal-free Synthesis of 2,4,5-Trisubstituted Pyridines and Pyridine N-Oxides by [2+2] Cycloaddition of Enaminones to Propyne Iminium Salts
- Propyne Iminium Salts and Isoquinoline – 1 : 1 and 2 : 1 Adducts
- A Direct Synthesis of a Strongly Zwitterionic 6,6'-Diaminofulvalene
- Neue aromatische Bisguanidin-Kupfer-Komplexe und ihre Anwendung in der ATRP / New Aromatic Bisguanidine Copper Complexes and Their Application in ATRP
- Investigation of Imidazol(in)ium-dithiocarboxylates as Sensors for the Detection of Mercury(II) and Silver(I) Ions
- Syntheses and Characterization of N-(Indolyl)pyridinium Salts and of Their Ylides
- Cu(I)-catalyzed [3+2] Cycloadditions of tert-Butyl (S)-(3-Oxopent-4- yn-2-yl)carbamate to 1-Benzylidenepyrazole-3-one-derived Azomethine Imines
- Zugänge zu Isomeren und Verwandten der Lamellarin-Alkaloide / Approach to Isomers and Structural Relatives of the Lamellarin Alkaloids
- Novel Dihydropyrazines and their Double ortho-Annulation to Hexaazapentacenes
Schlagwörter für diesen Artikel
1-Arylazo-2-naphthols;
Benzo[b]naphtho[2,1-e]thiazolo[2,3-c][1,2,4]triazinium Salts;
Naphtho[2,1-e]thiazolo[2,3-c][1,2,4]triazinium Salts;
Naphtho[2,1-e][1,3,4]thiadiazolo [2,3-c][1,3,4]triazinium Salts;
Vilsmeier Reaction
Artikel in diesem Heft
- Chemistry of Iminium Salts, Imines, and Related Compounds
- Thiaminpyrophosphat – ein natürlich vorkommendes Iminium-Salz. Seine Bedeutung für die mikrobiellen Prozesse bei der Weinbereitung und die Aromabildung im Wein / Thiamine Diphosphate – A Natural Iminium Salt. Its Role in Microbiological Processes During Wine Preparation and on the Aroma of Wine
- Formation of Azolo[1,2,4]triazinium Salts by Reaction of Heterocyclicsubstituted 1-Azo-naphthalen-2-ols with Strong Acids
- Synthesis of Methyl 3-Azidothieno[2,3-b]pyridine-2-carboxylates and Application of the Huisgen Reaction
- Orthoamide und Iminiumsalze, LXXXVII [1]. Eine neue, einfache Synthese für 1,3-Dimethylthymin / Orthoamides and Iminium Salts LXXXVII [1]. A New and Facile Synthesis of 1,3-Dimethylthymine
- Orthoamide und Iminiumsalze, LXXXIV [1]. Die Synthese von starken Formylierungsmitteln im präparativen Großmaßstab: Tris(dichlormethyl)amin / Orthoamides and Iminiumsalts LXXXIV [1]. The Synthesis of Strong Formylating Reagents on a Large Preparative Scale: Tris(chloromethyl)amine
- Orthoamide und Iminiumsalze, LXXXV [1]. Die Synthese von starken Formylierungsmitteln im präparativen Großmaßstab: N,N,N',N'- Tetraformylhydrazin und Formyl-aalen [Tris(diformylamino)methan] / Orthoamides and Iminium Salts LXXXV [1]. The Synthesis of Strong Formylating Reagents on a Large Preparative Scale: N;N;N';N'-Tetraformylhydrazine and Formyl-aalen [Tris(diformylamino)methane]
- Phenothiazine-Aromatic Hydrocarbon Acceptor Dyads as Photo-induced Electron Transfer Systems by Ugi Four-Component Reaction
- A Simple Metal-free Synthesis of 2,4,5-Trisubstituted Pyridines and Pyridine N-Oxides by [2+2] Cycloaddition of Enaminones to Propyne Iminium Salts
- Propyne Iminium Salts and Isoquinoline – 1 : 1 and 2 : 1 Adducts
- A Direct Synthesis of a Strongly Zwitterionic 6,6'-Diaminofulvalene
- Neue aromatische Bisguanidin-Kupfer-Komplexe und ihre Anwendung in der ATRP / New Aromatic Bisguanidine Copper Complexes and Their Application in ATRP
- Investigation of Imidazol(in)ium-dithiocarboxylates as Sensors for the Detection of Mercury(II) and Silver(I) Ions
- Syntheses and Characterization of N-(Indolyl)pyridinium Salts and of Their Ylides
- Cu(I)-catalyzed [3+2] Cycloadditions of tert-Butyl (S)-(3-Oxopent-4- yn-2-yl)carbamate to 1-Benzylidenepyrazole-3-one-derived Azomethine Imines
- Zugänge zu Isomeren und Verwandten der Lamellarin-Alkaloide / Approach to Isomers and Structural Relatives of the Lamellarin Alkaloids
- Novel Dihydropyrazines and their Double ortho-Annulation to Hexaazapentacenes