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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Synthesis of Hydroxypyrrolone Carboxamides Employing Selectfluor
Tim Carlo Allmann1, Rares-Petru Moldovan1, Peter G Jones2
1Institute of Organic Chemistry, Technical University Braunschweig, Hagenring 30, 38106 Braunschweig (Germany).
Abstract:
Reaction of pyrrole-2-carboxamides with Selectfluor in MeCN/water (4:1) affords 2-hydroxy-5-oxopyrrole-2-carboxamides in yields of up to 80 %. A variety of sensitive functional groups is tolerated, among them aldehydes and alkynes. The new method also works in the presence of allyl groups and appears to be superior to the use of singlet oxygen. Reaction of the monobrominated dihydropyrrolo[1,2-a]pyrazinone mukanadin C and its nonbrominated analogue afforded bicyclic hydroxypyrrolones. These compounds are interesting as they constitute a partial structure of the marine natural product oxocyclostylidol.
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