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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...

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Autores principales: Wang, Zhen-Hua, Zhang, Tong, Shen, Li-Wen, Yang, Xiu, Zhang, Yan-Ping, You, Yong, Zhao, Jian-Qiang, Yuan, Wei-Cheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
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.
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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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