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
© 1946 – 2014: Verlag der Zeitschrift für Naturforschung
                                        
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                                    Articles in the same Issue
- 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
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 - 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
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 - 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
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Keywords for this article
                        
                            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
                        
                    Articles in the same Issue
- 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