Cycloaddition of Aroyl Isothiocyanate: A Novel Synthesis of Triazine, Oxazine, Pyrimidine, and Pyridine Derivatives

A simple and direct synthetic methodology for a novel series of azines and their annulated systems was performed. Heterocyclization of acyl isothiocyanate 2 with urea or malononitrile gave s‐triazine 4 and 1,3‐oxazine 7 derivatives, respectively. The reaction of heteroallene 1 with acetylacetone tol...

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Veröffentlicht in:Journal of heterocyclic chemistry 2019-10, Vol.56 (10), p.2954-2959
Hauptverfasser: Assy, Mohamed G., El‐Sayed, Hassan A., Ouf, Nabil H., Hamza, Ahmed, Morsy, Hesham A.
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Sprache:eng
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Zusammenfassung:A simple and direct synthetic methodology for a novel series of azines and their annulated systems was performed. Heterocyclization of acyl isothiocyanate 2 with urea or malononitrile gave s‐triazine 4 and 1,3‐oxazine 7 derivatives, respectively. The reaction of heteroallene 1 with acetylacetone tolerated 2‐thioxopyridine derivative 9. The latter compound underwent heterocyclization with urea, hydrazine hydrate, or phenyl hydrazine to give the annulated pyridines 10–12. Pyrimidinethione 14 was resulted from reaction of acylisothiocyanate with enamine 13. Condensation of compound 14 with hydrazine hydrate, phenyl hydrazine, urea, and 3‐nitrobenzaldehyde in the presence of ethyl cyanoacetate or sodium hydroxide afforded 15–20, respectively.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3690