Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate

The reactivity of α-azidochalcones has been explored for the preparation of highly substituted oxazoles via a 2H-azirine intermediate. The azidochalcones, when treated with potassium thiocyanate in the presence of potassium persulfate, lead to 2,4,5-trisubstituted oxazoles in good yields. Incidental...

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Autores principales: Harisha, Mysore Bhyrappa, Dhanalakshmi, Pandi, Suresh, Rajendran, Kumar, Raju Ranjith, Muthusubramanian, Shanmugam
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7476590/
https://www.ncbi.nlm.nih.gov/pubmed/32952727
http://dx.doi.org/10.3762/bjoc.16.178
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author Harisha, Mysore Bhyrappa
Dhanalakshmi, Pandi
Suresh, Rajendran
Kumar, Raju Ranjith
Muthusubramanian, Shanmugam
author_facet Harisha, Mysore Bhyrappa
Dhanalakshmi, Pandi
Suresh, Rajendran
Kumar, Raju Ranjith
Muthusubramanian, Shanmugam
author_sort Harisha, Mysore Bhyrappa
collection PubMed
description The reactivity of α-azidochalcones has been explored for the preparation of highly substituted oxazoles via a 2H-azirine intermediate. The azidochalcones, when treated with potassium thiocyanate in the presence of potassium persulfate, lead to 2,4,5-trisubstituted oxazoles in good yields. Incidentally, 2-aminothiazoles are the products when ferric nitrate is employed instead of persulfate in the above reaction.
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spelling pubmed-74765902020-09-18 Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate Harisha, Mysore Bhyrappa Dhanalakshmi, Pandi Suresh, Rajendran Kumar, Raju Ranjith Muthusubramanian, Shanmugam Beilstein J Org Chem Full Research Paper The reactivity of α-azidochalcones has been explored for the preparation of highly substituted oxazoles via a 2H-azirine intermediate. The azidochalcones, when treated with potassium thiocyanate in the presence of potassium persulfate, lead to 2,4,5-trisubstituted oxazoles in good yields. Incidentally, 2-aminothiazoles are the products when ferric nitrate is employed instead of persulfate in the above reaction. Beilstein-Institut 2020-08-31 /pmc/articles/PMC7476590/ /pubmed/32952727 http://dx.doi.org/10.3762/bjoc.16.178 Text en Copyright © 2020, Harisha et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Harisha, Mysore Bhyrappa
Dhanalakshmi, Pandi
Suresh, Rajendran
Kumar, Raju Ranjith
Muthusubramanian, Shanmugam
Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate
title Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate
title_full Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate
title_fullStr Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate
title_full_unstemmed Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate
title_short Access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate
title_sort access to highly substituted oxazoles by the reaction of α-azidochalcone with potassium thiocyanate
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7476590/
https://www.ncbi.nlm.nih.gov/pubmed/32952727
http://dx.doi.org/10.3762/bjoc.16.178
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