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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Bibliographic Details
Published in:RSC advances 2022-03, Vol.12 (13), p.8263-8273
Main Authors: Chan, Chieh-Kai, Chung, Yi-Hsiu, Wang, Cheng-Chung
Format: Article
Language:English
Subjects:
Chemistry
Irradiation
Pyridines
Single crystals
Triflic acid
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Summary: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. A Kröhnke pyridine synthetic route towards functionalized TAPs and 3-benzyl TAPs has been established using TMSOTf/HMDS under microwave irradiation conditions.
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra00084a