Journal ArticleDOI
Antivirale Wirkstoffe. 5. Mitt. Das Benzo- 1,2,3-triazin-Ringsystem als Basis Potentiell virustatischer Verbindungen
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TLDR
The synthesis of 3]-1-adamantyl]-3,4-dihydro-4-oxo-benzo-[e]-1,2,3-triazine (7) containing a ring carboxylic acid amide grouping starts with 2-nitrobenzoic acid (1) which, after conversion into its acid chloride 2, is caused to react with 1-aminoadamantane (3) to give 2-nibbane (4), catalytic hydrogenation of 4 yields 2-amino-benAbstract:
Die Synthese des eine ringgebundene Carbonsaureamidgruppierung enthaltenden 3-[Admantyl-(1)]-3,4-dihydro-4-oxo-benzo[e]-1,2,3-triazins (7) nimmt ihren Ausgang in 2-Nitro-benzoesaure (1), die nach Uberfuhrung in ihr Saurechlorid 2 mit 1-Amino-adamantan (3) zu 2-Nitro-benzoesaure-[adamantyl-(1)]-amid (4) umgesetzt wird. Katalytische Hydrierung von 4 liefert 2-Aminobenzeosaure-[adamantyl-(1)]-amid (5). Uber das korrespondierende Diazoniumsalz 6 erfolgt Cyclisierung zu 7. Die unter der Einwirkung von Hydrazin und Raney-Nickel erfolgende Ringspaltung von 7 wird durch Bildung der Folgeprodukte 8, 10, 13 und 14 nachweisbar.
The Benzo-1,2,3-triazinc Ring System as Basis of Potentially Virustatic Compounds
The synthesis of 3-[1-adamantyl]-3,4-dihydro-4-oxo-benzo-[e]-1,2,3-triazine (7) containing a ring carboxylic acid amide grouping starts with 2-nitrobenzoic acid (1) which, after conversion into its acid chloride 2, is caused to react with 1-aminoadamantane (3) to give 2-nitrobenzoic acid-[1-adamantyl]-amide (4). Catalytic hydrogenation of 4 yields 2-amino-benzoic acid-[1-adamantyl]-amide (5). Cyclization to give 7 takes place via the corresponding diazonium salt 6. The ring cleavage occurring through the action of hydrazine and Raney nickel is substantiated by formation of the derivatives 8, 10, 13, and 14.read more
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Book ChapterDOI
3 The Medicinal Chemistry of 1,2,3-Triazines
TL;DR: A medicinally desirable diazonium compound would test the skills of the most talented pharmaceutical formulator because of the inherent instability of this structural type: fused 1,2,3-triazines on the other hand are, in general, stable crystalline compounds readily amenable to manipulation yet lacking little in chemical versatility.
Journal ArticleDOI
Heteryladamantanes: Synthetic Investigations of Recent Years, Biological Activity, and Other Aspects of Practical Application. (Review)
TL;DR: In this article, the first five years of published data of the last five years on methods for the synthesis of adamantyl-substituted heterocycles were analyzed and the biological activity and other practical applications of heteryladamantanes were reviewed for the first time.
Journal ArticleDOI
Adamantane derivatives containing heterocyclic substituents in the bridgehead positions. Synthesis and properties
TL;DR: In this article, the synthesis, transformations, and applications of adamantane derivatives containing heterocyclic substituents in the bridgehead positions are surveyed, described systematically, and analysed.
Journal ArticleDOI
Antimykotische Wirkstoffe, 4. Mitt.: Derivate tricyclischer Systeme durch Aminomethinylierung
TL;DR: The reaction of s-triazine (1) with 2-benzothiazolylguanidine (2) leads to 2-imino-2H-s-triazino-[2,1-b]benzin through 3 and 4 as intermediates as mentioned in this paper.
Journal ArticleDOI
Antivirale Wirkstoffe, 6. Mitt.: Substituentenvariation in der Reihe N′-substituierter N-[Adamantyl-(1)]-thioharnstoffe
TL;DR: In this article, the 1-Amino-adamantans (1) with isothiocyanates (IsothIoA) were used for the synthesis of N-[Adamantyl-(1)]-thioharnstoffe.
References
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Journal ArticleDOI
Cyanamid als NH-aktive komponente in der synthese von dehydro-N-mannich-basen
TL;DR: In this article, an H-aktiven Reaktionspartners ubernehmen in the Cyanamid are umsetzt in der Umsetzung einer H-AKtiven Verbindung with s-Triazin (2) and einem sekundaren Amin (5) beinhaltenden Dreikomponentenreaktion.