[3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions

The photodenitrogenation of vinyl azides to 2H-azirines by using a photoflow reactor is reported and compared with thermal formation of 2H-azirines. Photochemically, the ring of the 2H-azirines was opened to yield the nitrile ylides, which underwent a [3 + 2]-cycloaddition with 1,3-dipolarophiles. W...

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Autores principales: Cludius-Brandt, Stephan, Kupracz, Lukas, Kirschning, Andreas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778330/
https://www.ncbi.nlm.nih.gov/pubmed/24062837
http://dx.doi.org/10.3762/bjoc.9.201
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author Cludius-Brandt, Stephan
Kupracz, Lukas
Kirschning, Andreas
author_facet Cludius-Brandt, Stephan
Kupracz, Lukas
Kirschning, Andreas
author_sort Cludius-Brandt, Stephan
collection PubMed
description The photodenitrogenation of vinyl azides to 2H-azirines by using a photoflow reactor is reported and compared with thermal formation of 2H-azirines. Photochemically, the ring of the 2H-azirines was opened to yield the nitrile ylides, which underwent a [3 + 2]-cycloaddition with 1,3-dipolarophiles. When diisopropyl azodicarboxylate serves as the dipolarophile, 1,3,4-triazoles become directly accessible starting from the corresponding vinyl azide.
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spelling pubmed-37783302013-09-23 [3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions Cludius-Brandt, Stephan Kupracz, Lukas Kirschning, Andreas Beilstein J Org Chem Full Research Paper The photodenitrogenation of vinyl azides to 2H-azirines by using a photoflow reactor is reported and compared with thermal formation of 2H-azirines. Photochemically, the ring of the 2H-azirines was opened to yield the nitrile ylides, which underwent a [3 + 2]-cycloaddition with 1,3-dipolarophiles. When diisopropyl azodicarboxylate serves as the dipolarophile, 1,3,4-triazoles become directly accessible starting from the corresponding vinyl azide. Beilstein-Institut 2013-08-26 /pmc/articles/PMC3778330/ /pubmed/24062837 http://dx.doi.org/10.3762/bjoc.9.201 Text en Copyright © 2013, Cludius-Brandt et al. https://creativecommons.org/licenses/by/2.0https://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/2.0), 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
Cludius-Brandt, Stephan
Kupracz, Lukas
Kirschning, Andreas
[3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions
title [3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions
title_full [3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions
title_fullStr [3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions
title_full_unstemmed [3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions
title_short [3 + 2]-Cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions
title_sort [3 + 2]-cycloadditions of nitrile ylides after photoactivation of vinyl azides under flow conditions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778330/
https://www.ncbi.nlm.nih.gov/pubmed/24062837
http://dx.doi.org/10.3762/bjoc.9.201
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