Kyoto Pharmaceutical University.
Chem Pharm Bull (Tokyo). 2021;69(4):391-399. doi: 10.1248/cpb.c20-00993.
We have been interested in the reactivities of small-ring compounds and have reported reactions that proceed through cyclopropane intermediates starting from coumarin derivatives bearing an electron-withdrawing group at the 3-position or 2-oxo-2H-pyran-3-carboxylate derivatives and dimethylsulfoxonium methylide. This time, the reaction between 3-oxa-2-oxobicyclo[4.2.0]oct-4-ene-1-carboxylate and dimethylsulfoxonium methylide has been investigated. 3a,4,5,7a-Tetrahydro-7-hydroxybenzofuran-6-carboxylate and/or 2-hydroxybicyclo[4.1.0]hept-2-ene-3-carboxylate were obtained. The compounds were characterized using various spectral and X-ray crystallographic techniques. A plausible reaction mechanism has been discussed. This reaction was applied to some 3-oxa-2-oxobicyclo[4.2.0]oct-4-ene-1-carboxylate derivatives to clarify the generality.
我们一直对小环化合物的反应活性感兴趣，并报道了从 3-位带有吸电子基团的香豆素衍生物或 2-氧代-2H-吡喃-3-羧酸酯衍生物和二甲亚砜甲基叶立德出发，经过环丙烷中间体进行的反应。这次，我们研究了 3-氧杂-2-氧杂双环[4.2.0]辛-4-烯-1-羧酸酯与二甲亚砜甲基叶立德之间的反应。得到了 3a,4,5,7a-四氢-7-羟基苯并呋喃-6-羧酸酯和/或 2-羟基二环[4.1.0]庚-2-烯-3-羧酸酯。这些化合物使用各种光谱和 X 射线晶体学技术进行了表征。讨论了一种可能的反应机理。该反应应用于一些 3-氧杂-2-氧杂双环[4.2.0]辛-4-烯-1-羧酸酯衍生物，以阐明其普遍性。
