Kang Bubwoong, Ikeda Kaede
Graduate School of Agricultural Science, Kobe University.
Chem Pharm Bull (Tokyo). 2023 Apr 1;71(4):318-325. doi: 10.1248/cpb.c23-00068. Epub 2023 Feb 17.
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.
我们发现了用于水杨醛与丙烯腈环化缩合生成3-氰基-2H-色烯的优良碱介质，在过去二十年中该反应仅由1,4-二氮杂双环[2.2.2]辛烷（DABCO）介导。这些反应最有效地由4-二甲氨基吡啶（DMAP）介导，在大多数情况下，DMAP生成3-氰基-2H-色烯的产率高于DABCO。我们还证实，在使用催化量DMAP的十克规模实验中，该反应仍保持高产率。通过将得到的3-氰基-2H-色烯衍生化为已知的2H-色烯-3-羧酸，也例证了该反应的实用性，该2H-色烯-3-羧酸先前是用一种不易获得的试剂合成的。
