3 years ago

Furan Ring Opening – Pyridine Ring Closure: An Efficient Approach towards 6H-Isochromeno[4,3-b]pyridin-6-ones from Readily Available Furans and Phthalaldehydic Acid Methyl Esters

Furan Ring Opening – Pyridine Ring Closure: An Efficient Approach towards 6H-Isochromeno[4,3-b]pyridin-6-ones from Readily Available Furans and Phthalaldehydic Acid Methyl Esters
Maxim G. Uchuskin, Alexandra A. Kolodina, Pavel M. Shpuntov, Vladimir T. Abaev
An efficient iodine-catalyzed three-component Mannich-type reaction of various 2-alkylfurans, methyl 2-formylbenzoates and carbamates under mild reaction conditions was realized. Synthetic utility of the resulting N-Boc-1-[2-(carbomethoxy)aryl]furfurylamines was demonstrated by their facile two-step transformation into 2-methyl-6H-isochromeno[4,3-b]pyridin-6-ones, which are employed in high-performance cyclometalated OLEDs.Straightforward functionalization of furans by means of a three-component Mannich-type condensation reaction with methyl 2-formylbenzoates and carbamates was accomplished. The synthetic utility of the resultant N-Boc arylfurfurylamines was demonstrated by a practical two-step strategy that leads to 6H-isochromeno[4,3-b]pyridin-6-ones, which are used as cyclometalating ligands for OLEDs.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejoc.201701355

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