4.6 Article

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

期刊

RSC ADVANCES
卷 12, 期 13, 页码 8263-8273

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ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ra00084a

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  1. Academia Sinica [AS-TP-111-M01, AS-SUMMIT-110]
  2. Ministry of Science and Technology [MOST 110-2113-M-001-025-, MOST 110-2811-M-001-644-]
  3. Academia Sinica

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An efficient protocol using the TMSOTf/HMDS system for the intermolecular cyclization of chalcones under MW irradiation conditions has been developed. 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, a new core structure of 2,6-diazabicyclo[2.2.2]oct-2-ene was obtained by changing the acid additive to Sn(OTf)(2), which was confirmed by X-ray single-crystal diffraction analysis.
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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