cheminform abstract: an efficient one-step synthesis of piperidin-2-yl and pyrrolidin-2-yl flavonoid...

ChemInform 2012, 43, issue 19 © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Alkaloids U 0600 DOI: 10.1002/chin.201219211 An Efficient One-Step Synthesis of Piperidin-2-yl and Pyrrolidin-2-yl Flavonoid Alkaloids Through Phenolic Mannich Reactions. — The title reaction of chrysin (I) can be controlled by the conditions: simply running in a solvent mixture, the process affords C-6 substituted products, whereas in the presence of aqueous NaOH, C-8 sub- stitution takes place. The method can be extended to naphthols and simple phenols, which react with different imines in a completely regioselective manner. — (NGUYEN, T. B.; WANG*, Q.; GUERITTE, F.; Eur. J. Org. Chem. 2011, 35, 7076-7079, http://dx.doi.org/10.1002/ejoc.201101312 ; Cent. Rech. Gif, Inst. Chim. Subst. Nat., CNRS, F-91198 Gif-sur-Yvette, Fr.; Eng.) — Lindner 19- 211

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Page 1: ChemInform Abstract: An Efficient One-Step Synthesis of Piperidin-2-yl and Pyrrolidin-2-yl Flavonoid Alkaloids Through Phenolic Mannich Reactions

AlkaloidsU 0600 DOI: 10.1002/chin.201219211

An Efficient One-Step Synthesis of Piperidin-2-yl and Pyrrolidin-2-yl Flavonoid Alkaloids Through Phenolic Mannich Reactions. — The title reaction of chrysin (I) can be controlled by the conditions: simply running in a solvent mixture, the process affords C-6 substituted products, whereas in the presence of aqueous NaOH, C-8 sub-stitution takes place. The method can be extended to naphthols and simple phenols, which react with different imines in a completely regioselective manner. — (NGUYEN, T. B.; WANG*, Q.; GUERITTE, F.; Eur. J. Org. Chem. 2011, 35, 7076-7079, http://dx.doi.org/10.1002/ejoc.201101312 ; Cent. Rech. Gif, Inst. Chim. Subst. Nat., CNRS, F-91198 Gif-sur-Yvette, Fr.; Eng.) — Lindner

19- 211

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