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Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks
A convenient and efficient synthesis of novel achiral and chiral heterocyclic amino acid-like building blocks was developed. Regioisomeric methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates were prepared by the reaction of β-enamino ketoesters (including azetidine, pyrrolidine or piperidine ena...
| Autores principales: | , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2022
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8767561/ https://www.ncbi.nlm.nih.gov/pubmed/35096179 http://dx.doi.org/10.3762/bjoc.18.11 |
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| author | Bruzgulienė, Jolita Račkauskienė, Greta Bieliauskas, Aurimas Milišiūnaitė, Vaida Dagilienė, Miglė Matulevičiūtė, Gita Martynaitis, Vytas Krikštolaitytė, Sonata Sløk, Frank A Šačkus, Algirdas |
| author_facet | Bruzgulienė, Jolita Račkauskienė, Greta Bieliauskas, Aurimas Milišiūnaitė, Vaida Dagilienė, Miglė Matulevičiūtė, Gita Martynaitis, Vytas Krikštolaitytė, Sonata Sløk, Frank A Šačkus, Algirdas |
| author_sort | Bruzgulienė, Jolita |
| collection | PubMed |
| description | A convenient and efficient synthesis of novel achiral and chiral heterocyclic amino acid-like building blocks was developed. Regioisomeric methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates were prepared by the reaction of β-enamino ketoesters (including azetidine, pyrrolidine or piperidine enamines) with hydroxylamine hydrochloride. Unambiguous structural assignments were based on chiral HPLC analysis, (1)H, (13)C, and (15)N NMR spectroscopy, HRMS, and single-crystal X-ray diffraction data. |
| format | Online Article Text |
| id | pubmed-8767561 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2022 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-87675612022-01-27 Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks Bruzgulienė, Jolita Račkauskienė, Greta Bieliauskas, Aurimas Milišiūnaitė, Vaida Dagilienė, Miglė Matulevičiūtė, Gita Martynaitis, Vytas Krikštolaitytė, Sonata Sløk, Frank A Šačkus, Algirdas Beilstein J Org Chem Full Research Paper A convenient and efficient synthesis of novel achiral and chiral heterocyclic amino acid-like building blocks was developed. Regioisomeric methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates were prepared by the reaction of β-enamino ketoesters (including azetidine, pyrrolidine or piperidine enamines) with hydroxylamine hydrochloride. Unambiguous structural assignments were based on chiral HPLC analysis, (1)H, (13)C, and (15)N NMR spectroscopy, HRMS, and single-crystal X-ray diffraction data. Beilstein-Institut 2022-01-12 /pmc/articles/PMC8767561/ /pubmed/35096179 http://dx.doi.org/10.3762/bjoc.18.11 Text en Copyright © 2022, Bruzgulienė et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material. |
| spellingShingle | Full Research Paper Bruzgulienė, Jolita Račkauskienė, Greta Bieliauskas, Aurimas Milišiūnaitė, Vaida Dagilienė, Miglė Matulevičiūtė, Gita Martynaitis, Vytas Krikštolaitytė, Sonata Sløk, Frank A Šačkus, Algirdas Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks |
| title | Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks |
| title_full | Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks |
| title_fullStr | Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks |
| title_full_unstemmed | Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks |
| title_short | Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks |
| title_sort | regioselective synthesis of methyl 5-(n-boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8767561/ https://www.ncbi.nlm.nih.gov/pubmed/35096179 http://dx.doi.org/10.3762/bjoc.18.11 |
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