Serendipitous Formation of 2H-Pyrazolo[3,4-d]pyridazin-7(6H)-ones from 3-Arylsydnones

[Image: see text] Fused nitrogen heterocyclesnamely, pyrazolo[3,4-d]pyridazin-7(6H)-ones have been obtained by exploiting the 1,3-dipolar nature of N-arylsydnones, from hydrazones of 3-aryl-4-acetylsydnones via the Vilsmeier–Haack strategy. Facile intramolecular nucleophilic addition followed by CO(...

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Detalles Bibliográficos
Autores principales: Kumbar, Mahadev N., Shaikh, Saba Kauser J., Kamble, Ravindra R., Bayannavar, Praveen K., Kamble, Atulkumar A., Hunnur, Raveendra K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6647958/
https://www.ncbi.nlm.nih.gov/pubmed/31459679
http://dx.doi.org/10.1021/acsomega.8b02013
Descripción
Sumario:[Image: see text] Fused nitrogen heterocyclesnamely, pyrazolo[3,4-d]pyridazin-7(6H)-ones have been obtained by exploiting the 1,3-dipolar nature of N-arylsydnones, from hydrazones of 3-aryl-4-acetylsydnones via the Vilsmeier–Haack strategy. Facile intramolecular nucleophilic addition followed by CO(2) elimination under reflux or upon microwave irradiation was presented. Plausible mechanisms for the formation of the title compounds are proffered. Structure confirmatory evidence came from single-crystal X-ray crystallography.

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