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Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins
A practical three-step protocol for the assembly of triazolobenzodiazepine-fused diketopiperazines and hydantoins has been developed. The synthesis of these tetracyclic ring systems was initiated by an Ugi reaction, which brought together all necessary functionalities for further transformations. Th...
| Autores principales: | , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
Beilstein-Institut
2018
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| Materias: | |
| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870159/ https://www.ncbi.nlm.nih.gov/pubmed/29623124 http://dx.doi.org/10.3762/bjoc.14.49 |
| _version_ | 1783309419192254464 |
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| author | Vroemans, Robby Bamba, Fante Winters, Jonas Thomas, Joice Jacobs, Jeroen Van Meervelt, Luc John, Jubi Dehaen, Wim |
| author_facet | Vroemans, Robby Bamba, Fante Winters, Jonas Thomas, Joice Jacobs, Jeroen Van Meervelt, Luc John, Jubi Dehaen, Wim |
| author_sort | Vroemans, Robby |
| collection | PubMed |
| description | A practical three-step protocol for the assembly of triazolobenzodiazepine-fused diketopiperazines and hydantoins has been developed. The synthesis of these tetracyclic ring systems was initiated by an Ugi reaction, which brought together all necessary functionalities for further transformations. The Ugi adducts were then subjected to a base-induced ring closing and an intramolecular azide–alkyne cycloaddition reaction in succession to obtain highly fused benzodiazepine frameworks. |
| format | Online Article Text |
| id | pubmed-5870159 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2018 |
| publisher | Beilstein-Institut |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-58701592018-04-05 Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins Vroemans, Robby Bamba, Fante Winters, Jonas Thomas, Joice Jacobs, Jeroen Van Meervelt, Luc John, Jubi Dehaen, Wim Beilstein J Org Chem Full Research Paper A practical three-step protocol for the assembly of triazolobenzodiazepine-fused diketopiperazines and hydantoins has been developed. The synthesis of these tetracyclic ring systems was initiated by an Ugi reaction, which brought together all necessary functionalities for further transformations. The Ugi adducts were then subjected to a base-induced ring closing and an intramolecular azide–alkyne cycloaddition reaction in succession to obtain highly fused benzodiazepine frameworks. Beilstein-Institut 2018-03-14 /pmc/articles/PMC5870159/ /pubmed/29623124 http://dx.doi.org/10.3762/bjoc.14.49 Text en Copyright © 2018, Vroemans 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 Vroemans, Robby Bamba, Fante Winters, Jonas Thomas, Joice Jacobs, Jeroen Van Meervelt, Luc John, Jubi Dehaen, Wim Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins |
| title | Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins |
| title_full | Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins |
| title_fullStr | Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins |
| title_full_unstemmed | Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins |
| title_short | Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins |
| title_sort | sequential ugi reaction/base-induced ring closing/iaac protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins |
| topic | Full Research Paper |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5870159/ https://www.ncbi.nlm.nih.gov/pubmed/29623124 http://dx.doi.org/10.3762/bjoc.14.49 |
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