Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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4-Dimethylaminopyridine (DMAP), A Superior Mediator for Morita–Balylis–Hillman Reaction-Triggered Annulative Condensation of Salicylaldehydes and Acrylonitrile to Form 3-Cyano-2H-chromenes
Bubwoong Kang Kaede Ikeda
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2023 年 71 巻 4 号 p. 318-325

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We unveiled superior base mediators for the annulative condensation of salicylaldehydes and acrylonitrile to give 3-cyano-2H-chromenes, which has been mediated only by 1,4-diazabicyclo[2.2.2]octane (DABCO) over the past two decades. The reactions were most efficiently mediated by 4-dimethylaminopyridine (DMAP), which yielded 3-cyano-2H-chromenes in higher yields than DABCO in most cases. We also confirmed that the reaction remained high yielding in a decagram-scale experiment with a catalytic amount of DMAP. The utility of this reaction was also exemplified by derivatization of an obtained 3-cyano-2H-chromene into a known 2H-chromene-3-carboxylic acid, which was previously synthesized with a non-readily available reagent.

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© 2023 The Pharmaceutical Society of Japan
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