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Licensed Unlicensed Requires Authentication Published by De Gruyter June 2, 2014

Novel Dihydropyrazines and their Double ortho-Annulation to Hexaazapentacenes

  • Rainer Strathausen , Rainer Beckert EMAIL logo , Jan Fleischhauer , Dirk Müller and Helmar Görls
From the journal Zeitschrift für Naturforschung B
https://doi.org/10.5560/znb.2014-4002

The cycloacylation of oxalic amidines 7 with bis-imidoylchlorides 6 furnished the dihydropyrazine derivatives 8. Due to their vicinal amino-imino substructures, they provide good preconditions for a double intramolecular ring closure reaction. An alternative synthesis for hexaaza-pentacenes 1 was developed using potassium carbonate as the base and lead tetraacetate as the oxidizing agent.

Graphical Abstract

Novel Dihydropyrazines and their Double ortho-Annulation to Hexaazapentacenes

Novel Dihydropyrazines and their Double ortho-Annulation to Hexaazapentacenes

Keywords: Hexaazapentacenes; Dihydropyrazines; ortho-Annulation; Amidines; Fluorophores
Received: 2014-1-8
Published Online: 2014-6-2
Published in Print: 2014-5-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

From the journal
Zeitschrift für Naturforschung B
Zeitschrift für Naturforschung B
Volume 69 Issue 5

Journal and Issue

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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
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