Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, Chattar Manzil Palace, Lucknow-226 001, UP, India.
J Org Chem. 2013 Jun 21;78(12):5878-88. doi: 10.1021/jo400499r. Epub 2013 Jun 3.
A convenient and general synthesis of various 4-substituted 3-iodocoumarins and 4,5-disubstituted 3-iodobutenolides is described via an exclusive 6-endo-dig iodocyclization of 3-ethoxy-1-(2-alkoxyphenyl)-2-yn-1-ols and 5-endo-dig iodocyclization of 1-alkoxy-4-ethoxy-3-yn-1,2-diols, respectively. The reaction is carried out under very mild conditions using I2 in CH2Cl2 or toluene at room temperature. Oxygens in OMe and OMOM groups were used as efficient nucleophiles for this intramolecular cyclization to obtain the products in good to excellent yields.
描述了一种通过 3-乙氧基-1-(2-烷氧基苯基)-2-炔-1-醇的专属 6-endo-dig 碘环化反应和 1-烷氧基-4-乙氧基-3-炔-1,2-二醇的 5-endo-dig 碘环化反应，分别简便、通用地合成了各种 4-取代的 3-碘香豆素和 4,5-二取代的 3-碘丁烯内酯。该反应在非常温和的条件下，使用 I2 在 CH2Cl2 或甲苯中于室温下进行。OMe 和 OMOM 基团中的氧作为有效的亲核试剂，用于此分子内环化反应，以良好至优异的收率获得产物。
