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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Detalles Bibliográficos
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
Descripción
Sumario: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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