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Neue Synthesen von 1,3-Oxazinen, Thiazolen und 1,2-Dithiolen

✍ Scribed by Capuano, Lilly ;Bolz, Gerda ;Burger, Robert ;Burkhardt, Volker ;Huch, Volker

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
491 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

New Syntheses of 1,3‐Oxazines, Thiazoles, and 1,2‐Dithioles

The 2‐diazo‐1,3‐diketones 1 react with thioamides 4 via the acyl ketenes 3, resulting from Wolff rearrangement, to give the 1,3‐oxazine‐4‐ones 10; however, by increasing the electro‐philicity of the diazo compounds or the nucleophilicity of the thioamides, the 5‐acylthiazoles 9 are obtained. These are derived from the diketocarbene intermediates 2. The structure of 9g was confirmed by X‐ray diffraction analysis. — The best preparative method for 1,3‐oxazinones consists in the dehydratation of the 2,N‐diacylacetamides 8, which are readily available from the reaction of diazodiketones with carboxamides. — The thionation of 8 or 10 with P~4~S~10~ proceeds with spontaneous dehydrogenation, affording high yields of 3‐(thiobenzoylimido)‐1,2‐dithioles 15. The structure of 15a was established by X‐ray diffraction analysis.

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Synthesen von Thiazolo- und [1,3]Thiazin
Synthesen von Thiazolo- und [1,3]Thiazino[1,2,4]triazinonen
✍ Arndt, Friedrich ;Franke, Wilfried ;Klose, Walter ;Lorenz, Jörg ;Schwarz, Katica 📂 Article 📅 1984 🏛 John Wiley and Sons 🌐 English ⚖ 275 KB

## Abstract Es werden die Synthesen der Thiazolo‐ und [1,3]Thiazino[1,2,4]triazinone **3**–**6** beschrieben. Die Darstellungen der Verbindungen **3** und **5** gelangen regiospezifisch mittels der Verbindungen **12** und **13**.