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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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
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author Kumbar, Mahadev N.
Shaikh, Saba Kauser J.
Kamble, Ravindra R.
Bayannavar, Praveen K.
Kamble, Atulkumar A.
Hunnur, Raveendra K.
author_facet Kumbar, Mahadev N.
Shaikh, Saba Kauser J.
Kamble, Ravindra R.
Bayannavar, Praveen K.
Kamble, Atulkumar A.
Hunnur, Raveendra K.
author_sort Kumbar, Mahadev N.
collection PubMed
description [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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spelling pubmed-66479582019-08-27 Serendipitous Formation of 2H-Pyrazolo[3,4-d]pyridazin-7(6H)-ones from 3-Arylsydnones Kumbar, Mahadev N. Shaikh, Saba Kauser J. Kamble, Ravindra R. Bayannavar, Praveen K. Kamble, Atulkumar A. Hunnur, Raveendra K. ACS Omega [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. American Chemical Society 2019-03-06 /pmc/articles/PMC6647958/ /pubmed/31459679 http://dx.doi.org/10.1021/acsomega.8b02013 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Kumbar, Mahadev N.
Shaikh, Saba Kauser J.
Kamble, Ravindra R.
Bayannavar, Praveen K.
Kamble, Atulkumar A.
Hunnur, Raveendra K.
Serendipitous Formation of 2H-Pyrazolo[3,4-d]pyridazin-7(6H)-ones from 3-Arylsydnones
title Serendipitous Formation of 2H-Pyrazolo[3,4-d]pyridazin-7(6H)-ones from 3-Arylsydnones
title_full Serendipitous Formation of 2H-Pyrazolo[3,4-d]pyridazin-7(6H)-ones from 3-Arylsydnones
title_fullStr Serendipitous Formation of 2H-Pyrazolo[3,4-d]pyridazin-7(6H)-ones from 3-Arylsydnones
title_full_unstemmed Serendipitous Formation of 2H-Pyrazolo[3,4-d]pyridazin-7(6H)-ones from 3-Arylsydnones
title_short Serendipitous Formation of 2H-Pyrazolo[3,4-d]pyridazin-7(6H)-ones from 3-Arylsydnones
title_sort serendipitous formation of 2h-pyrazolo[3,4-d]pyridazin-7(6h)-ones from 3-arylsydnones
url 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
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