Continuous multistep synthesis of 2-(azidomethyl)oxazoles
An efficient three-step protocol was developed to produce 2-(azidomethyl)oxazoles from vinyl azides in a continuous-flow process. The general synthetic strategy involves a thermolysis of vinyl azides to generate azirines, which react with bromoacetyl bromide to provide 2-(bromomethyl)oxazoles. The l...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.36 |
| _version_ | 1818369255431733248 |
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| author | Thaís A. Rossa Nícolas S. Suveges Marcus M. Sá David Cantillo C. Oliver Kappe |
| author_facet | Thaís A. Rossa Nícolas S. Suveges Marcus M. Sá David Cantillo C. Oliver Kappe |
| author_sort | Thaís A. Rossa |
| collection | DOAJ |
| description | An efficient three-step protocol was developed to produce 2-(azidomethyl)oxazoles from vinyl azides in a continuous-flow process. The general synthetic strategy involves a thermolysis of vinyl azides to generate azirines, which react with bromoacetyl bromide to provide 2-(bromomethyl)oxazoles. The latter compounds are versatile building blocks for nucleophilic displacement reactions as demonstrated by their subsequent treatment with NaN3 in aqueous medium to give azido oxazoles in good selectivity. Process integration enabled the synthesis of this useful moiety in short overall residence times (7 to 9 min) and in good overall yields. |
| first_indexed | 2024-12-13T23:20:56Z |
| format | Article |
| id | doaj.art-142e6c90c992459c85d56480bcacfd27 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-13T23:20:56Z |
| publishDate | 2018-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-142e6c90c992459c85d56480bcacfd272022-12-21T23:27:45ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-02-0114150651410.3762/bjoc.14.361860-5397-14-36Continuous multistep synthesis of 2-(azidomethyl)oxazolesThaís A. Rossa0Nícolas S. Suveges1Marcus M. Sá2David Cantillo3C. Oliver Kappe4Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, 8010 Graz, AustriaChemistry Institute, Federal University of Rio de Janeiro, Rio de Janeiro, RJ, Brazil 22941-909,Departamento de Quıímica, Universidade Federal de Santa Catarina, Florianópolis 88040-900, SC, BrazilInstitute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, 8010 Graz, AustriaInstitute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, 8010 Graz, AustriaAn efficient three-step protocol was developed to produce 2-(azidomethyl)oxazoles from vinyl azides in a continuous-flow process. The general synthetic strategy involves a thermolysis of vinyl azides to generate azirines, which react with bromoacetyl bromide to provide 2-(bromomethyl)oxazoles. The latter compounds are versatile building blocks for nucleophilic displacement reactions as demonstrated by their subsequent treatment with NaN3 in aqueous medium to give azido oxazoles in good selectivity. Process integration enabled the synthesis of this useful moiety in short overall residence times (7 to 9 min) and in good overall yields.https://doi.org/10.3762/bjoc.14.36azirinescontinuous flowheterocyclesoxazolesprocess integrationvinyl azides |
| spellingShingle | Thaís A. Rossa Nícolas S. Suveges Marcus M. Sá David Cantillo C. Oliver Kappe Continuous multistep synthesis of 2-(azidomethyl)oxazoles Beilstein Journal of Organic Chemistry azirines continuous flow heterocycles oxazoles process integration vinyl azides |
| title | Continuous multistep synthesis of 2-(azidomethyl)oxazoles |
| title_full | Continuous multistep synthesis of 2-(azidomethyl)oxazoles |
| title_fullStr | Continuous multistep synthesis of 2-(azidomethyl)oxazoles |
| title_full_unstemmed | Continuous multistep synthesis of 2-(azidomethyl)oxazoles |
| title_short | Continuous multistep synthesis of 2-(azidomethyl)oxazoles |
| title_sort | continuous multistep synthesis of 2 azidomethyl oxazoles |
| topic | azirines continuous flow heterocycles oxazoles process integration vinyl azides |
| url | https://doi.org/10.3762/bjoc.14.36 |
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