TMSOTf-mediated Kröhnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation

An efficient protocol for the preparation of pyridine skeletons has been successfully developed involving the TMSOTf/HMDS (trifluoromethanesulfonic acid/hexamethyldisilane) system for the intermolecular cyclization of chalcones under MW (microwave) irradiation conditions. This method provides a faci...

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Autores principales: Chan, Chieh-Kai, Chung, Yi-Hsiu, Wang, Cheng-Chung
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2022
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8982443/
https://www.ncbi.nlm.nih.gov/pubmed/35424740
http://dx.doi.org/10.1039/d2ra00084a
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author Chan, Chieh-Kai
Chung, Yi-Hsiu
Wang, Cheng-Chung
author_facet Chan, Chieh-Kai
Chung, Yi-Hsiu
Wang, Cheng-Chung
author_sort Chan, Chieh-Kai
collection PubMed
description An efficient protocol for the preparation of pyridine skeletons has been successfully developed involving the TMSOTf/HMDS (trifluoromethanesulfonic acid/hexamethyldisilane) system for the intermolecular cyclization of chalcones under MW (microwave) irradiation conditions. This method provides a facile approach to synthesize 2,4,6-triaryl or 3-benzyl-2,4,6-triarylpyridines in good to excellent yields. Interestingly, the 2,6-diazabicyclo[2.2.2]oct-2-ene core was obtained by changing the acid additive to Sn(OTf)(2), and the desired product was also confirmed using X-ray single-crystal diffraction analysis.
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spelling pubmed-89824432022-04-13 TMSOTf-mediated Kröhnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation Chan, Chieh-Kai Chung, Yi-Hsiu Wang, Cheng-Chung RSC Adv Chemistry An efficient protocol for the preparation of pyridine skeletons has been successfully developed involving the TMSOTf/HMDS (trifluoromethanesulfonic acid/hexamethyldisilane) system for the intermolecular cyclization of chalcones under MW (microwave) irradiation conditions. This method provides a facile approach to synthesize 2,4,6-triaryl or 3-benzyl-2,4,6-triarylpyridines in good to excellent yields. Interestingly, the 2,6-diazabicyclo[2.2.2]oct-2-ene core was obtained by changing the acid additive to Sn(OTf)(2), and the desired product was also confirmed using X-ray single-crystal diffraction analysis. The Royal Society of Chemistry 2022-03-15 /pmc/articles/PMC8982443/ /pubmed/35424740 http://dx.doi.org/10.1039/d2ra00084a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Chan, Chieh-Kai
Chung, Yi-Hsiu
Wang, Cheng-Chung
TMSOTf-mediated Kröhnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation
title TMSOTf-mediated Kröhnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation
title_full TMSOTf-mediated Kröhnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation
title_fullStr TMSOTf-mediated Kröhnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation
title_full_unstemmed TMSOTf-mediated Kröhnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation
title_short TMSOTf-mediated Kröhnke pyridine synthesis using HMDS as the nitrogen source under microwave irradiation
title_sort tmsotf-mediated kröhnke pyridine synthesis using hmds as the nitrogen source under microwave irradiation
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8982443/
https://www.ncbi.nlm.nih.gov/pubmed/35424740
http://dx.doi.org/10.1039/d2ra00084a
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AT wangchengchung tmsotfmediatedkrohnkepyridinesynthesisusinghmdsasthenitrogensourceundermicrowaveirradiation

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