From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis

Heteroaromatic carboxylic acids have been directly coupled with imines using propylphosphonic anhydride (T3P) and NEt(iPr)(2) to form azaspirocycles via intermediate N‐acyliminium ions. Spirocyclic indolenines (3H‐indoles), azaindolenines, 2H‐pyrroles and 3H‐pyrroles were all accessed using this met...

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Autores principales: Chambers, Sarah J., Coulthard, Graeme, Unsworth, William P., O'Brien, Peter, Taylor, Richard J. K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5071705/
https://www.ncbi.nlm.nih.gov/pubmed/26918778
http://dx.doi.org/10.1002/chem.201600823
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author Chambers, Sarah J.
Coulthard, Graeme
Unsworth, William P.
O'Brien, Peter
Taylor, Richard J. K.
author_facet Chambers, Sarah J.
Coulthard, Graeme
Unsworth, William P.
O'Brien, Peter
Taylor, Richard J. K.
author_sort Chambers, Sarah J.
collection PubMed
description Heteroaromatic carboxylic acids have been directly coupled with imines using propylphosphonic anhydride (T3P) and NEt(iPr)(2) to form azaspirocycles via intermediate N‐acyliminium ions. Spirocyclic indolenines (3H‐indoles), azaindolenines, 2H‐pyrroles and 3H‐pyrroles were all accessed using this metal‐free approach. The reactions typically proceed with high diastereoselectivity and 3D shape analysis confirms that the products formed occupy areas of chemical space that are under‐represented in existing drugs and high throughput screening libraries.
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spelling pubmed-50717052016-11-02 From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis Chambers, Sarah J. Coulthard, Graeme Unsworth, William P. O'Brien, Peter Taylor, Richard J. K. Chemistry Communications Heteroaromatic carboxylic acids have been directly coupled with imines using propylphosphonic anhydride (T3P) and NEt(iPr)(2) to form azaspirocycles via intermediate N‐acyliminium ions. Spirocyclic indolenines (3H‐indoles), azaindolenines, 2H‐pyrroles and 3H‐pyrroles were all accessed using this metal‐free approach. The reactions typically proceed with high diastereoselectivity and 3D shape analysis confirms that the products formed occupy areas of chemical space that are under‐represented in existing drugs and high throughput screening libraries. John Wiley and Sons Inc. 2016-03-23 2016-05-04 /pmc/articles/PMC5071705/ /pubmed/26918778 http://dx.doi.org/10.1002/chem.201600823 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Chambers, Sarah J.
Coulthard, Graeme
Unsworth, William P.
O'Brien, Peter
Taylor, Richard J. K.
From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis
title From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis
title_full From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis
title_fullStr From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis
title_full_unstemmed From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis
title_short From Heteroaromatic Acids and Imines to Azaspirocycles: Stereoselective Synthesis and 3D Shape Analysis
title_sort from heteroaromatic acids and imines to azaspirocycles: stereoselective synthesis and 3d shape analysis
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5071705/
https://www.ncbi.nlm.nih.gov/pubmed/26918778
http://dx.doi.org/10.1002/chem.201600823
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