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Copper-catalyzed [3 + 2 + 1] annulation for functionalized pyridines as potent and dynamic UV absorbers†
Shizuka Mei Bautista Maezono,Sung Hong Kim,Yong Rok Lee
Organic Chemistry Frontiers Pub Date : 09/10/2018 00:00:00 , DOI:10.1039/C8QO00782A
Abstract

A novel Cu(OTf)2-catalyzed [3 + 2 + 1] annulation of chromenone carbaldehydes or benzochromenone carbaldehydes with β-enamino substrates and ammonium acetate is developed. This protocol provides a facile and efficient one-pot procedure for the construction of diverse and functionalized pyridines bearing a variety of substituents. This [3 + 2 + 1] annulation proceeds via a cascade aldol-type reaction, deprotonation and protonation, Michael addition and ring opening, and intramolecular Michael addition and heteroaromatization. The synthesized compounds exhibited potent and dynamic UV absorption for broad spectrum coverage.

Graphical abstract: Copper-catalyzed [3 + 2 + 1] annulation for functionalized pyridines as potent and dynamic UV absorbers
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