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Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N-Ylides and Electron-Deficient Olefins
[3 + 2] Cycloaddition reactions of heteroaromatic N-ylides with electron-deficient olefins have been developed. The heteroaromatic N-ylides, in situ generated from N-phenacylbenzothiazolium bromides, can smoothly react with maleimides under very mild conditions, affording fused polycyclic octahydrop...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10254280/ https://www.ncbi.nlm.nih.gov/pubmed/37298885 http://dx.doi.org/10.3390/molecules28114410 |
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author | Wang, Zhen-Hua Zhang, Tong Shen, Li-Wen Yang, Xiu Zhang, Yan-Ping You, Yong Zhao, Jian-Qiang Yuan, Wei-Cheng |
author_facet | Wang, Zhen-Hua Zhang, Tong Shen, Li-Wen Yang, Xiu Zhang, Yan-Ping You, Yong Zhao, Jian-Qiang Yuan, Wei-Cheng |
author_sort | Wang, Zhen-Hua |
collection | PubMed |
description | [3 + 2] Cycloaddition reactions of heteroaromatic N-ylides with electron-deficient olefins have been developed. The heteroaromatic N-ylides, in situ generated from N-phenacylbenzothiazolium bromides, can smoothly react with maleimides under very mild conditions, affording fused polycyclic octahydropyrrolo[3,4-c]pyrroles in good-to-excellent isolated yields. This reaction concept could also be extended to 3-trifluoroethylidene oxindoles and benzylidenemalononitriles as electron-deficient olefins for accessing highly functionalized polyheterocyclic compounds. A gram-scale experiment was also carried out to verify the practicability of the methodology. |
format | Online Article Text |
id | pubmed-10254280 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-102542802023-06-10 Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N-Ylides and Electron-Deficient Olefins Wang, Zhen-Hua Zhang, Tong Shen, Li-Wen Yang, Xiu Zhang, Yan-Ping You, Yong Zhao, Jian-Qiang Yuan, Wei-Cheng Molecules Article [3 + 2] Cycloaddition reactions of heteroaromatic N-ylides with electron-deficient olefins have been developed. The heteroaromatic N-ylides, in situ generated from N-phenacylbenzothiazolium bromides, can smoothly react with maleimides under very mild conditions, affording fused polycyclic octahydropyrrolo[3,4-c]pyrroles in good-to-excellent isolated yields. This reaction concept could also be extended to 3-trifluoroethylidene oxindoles and benzylidenemalononitriles as electron-deficient olefins for accessing highly functionalized polyheterocyclic compounds. A gram-scale experiment was also carried out to verify the practicability of the methodology. MDPI 2023-05-29 /pmc/articles/PMC10254280/ /pubmed/37298885 http://dx.doi.org/10.3390/molecules28114410 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Wang, Zhen-Hua Zhang, Tong Shen, Li-Wen Yang, Xiu Zhang, Yan-Ping You, Yong Zhao, Jian-Qiang Yuan, Wei-Cheng Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N-Ylides and Electron-Deficient Olefins |
title | Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N-Ylides and Electron-Deficient Olefins |
title_full | Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N-Ylides and Electron-Deficient Olefins |
title_fullStr | Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N-Ylides and Electron-Deficient Olefins |
title_full_unstemmed | Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N-Ylides and Electron-Deficient Olefins |
title_short | Diverse Synthesis of Fused Polyheterocyclic Compounds via [3 + 2] Cycloaddition of In Situ-Generated Heteroaromatic N-Ylides and Electron-Deficient Olefins |
title_sort | diverse synthesis of fused polyheterocyclic compounds via [3 + 2] cycloaddition of in situ-generated heteroaromatic n-ylides and electron-deficient olefins |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10254280/ https://www.ncbi.nlm.nih.gov/pubmed/37298885 http://dx.doi.org/10.3390/molecules28114410 |
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