Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

The synthesis of sydnones heteroarylated at C-4 with an indolizine was achieved by Chichibabin (Tschitschibabin) indolizine synthesis starting from the corresponding sydnone-N-pyridinium bromides. The latter compounds were also transformed to sydnone-indolizines connected through a keto group at the...

Descripción completa

Detalles Bibliográficos
Autores principales: Albota, Florin, Caira, Mino R, Draghici, Constantin, Dumitrascu, Florea, Dumitrescu, Denisa E
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238577/
https://www.ncbi.nlm.nih.gov/pubmed/28144319
http://dx.doi.org/10.3762/bjoc.12.245
_version_ 1782495729440260096
author Albota, Florin
Caira, Mino R
Draghici, Constantin
Dumitrascu, Florea
Dumitrescu, Denisa E
author_facet Albota, Florin
Caira, Mino R
Draghici, Constantin
Dumitrascu, Florea
Dumitrescu, Denisa E
author_sort Albota, Florin
collection PubMed
description The synthesis of sydnones heteroarylated at C-4 with an indolizine was achieved by Chichibabin (Tschitschibabin) indolizine synthesis starting from the corresponding sydnone-N-pyridinium bromides. The latter compounds were also transformed to sydnone-indolizines connected through a keto group at the C-4 position by refluxing them in 1,2-epoxybutane with an activated alkyne. The structures of the new compounds were assigned by FTIR, NMR spectroscopy and X-ray analysis.
format Online
Article
Text
id pubmed-5238577
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-52385772017-01-31 Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis Albota, Florin Caira, Mino R Draghici, Constantin Dumitrascu, Florea Dumitrescu, Denisa E Beilstein J Org Chem Full Research Paper The synthesis of sydnones heteroarylated at C-4 with an indolizine was achieved by Chichibabin (Tschitschibabin) indolizine synthesis starting from the corresponding sydnone-N-pyridinium bromides. The latter compounds were also transformed to sydnone-indolizines connected through a keto group at the C-4 position by refluxing them in 1,2-epoxybutane with an activated alkyne. The structures of the new compounds were assigned by FTIR, NMR spectroscopy and X-ray analysis. Beilstein-Institut 2016-11-23 /pmc/articles/PMC5238577/ /pubmed/28144319 http://dx.doi.org/10.3762/bjoc.12.245 Text en Copyright © 2016, Albota 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), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. 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
Albota, Florin
Caira, Mino R
Draghici, Constantin
Dumitrascu, Florea
Dumitrescu, Denisa E
Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis
title Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis
title_full Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis
title_fullStr Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis
title_full_unstemmed Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis
title_short Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis
title_sort sydnone c-4 heteroarylation with an indolizine ring via chichibabin indolizine synthesis
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238577/
https://www.ncbi.nlm.nih.gov/pubmed/28144319
http://dx.doi.org/10.3762/bjoc.12.245
work_keys_str_mv AT albotaflorin sydnonec4heteroarylationwithanindolizineringviachichibabinindolizinesynthesis
AT cairaminor sydnonec4heteroarylationwithanindolizineringviachichibabinindolizinesynthesis
AT draghiciconstantin sydnonec4heteroarylationwithanindolizineringviachichibabinindolizinesynthesis
AT dumitrascuflorea sydnonec4heteroarylationwithanindolizineringviachichibabinindolizinesynthesis
AT dumitrescudenisae sydnonec4heteroarylationwithanindolizineringviachichibabinindolizinesynthesis

Ejemplares similares