Organic Chemistry Section, Chemical Science and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR) , Trivandrum, Kerala 695019, India.
J Org Chem. 2016 Dec 2;81(23):11909-11915. doi: 10.1021/acs.joc.6b02367. Epub 2016 Nov 18.
A facile and efficient InCl catalyzed one-pot synthesis of highly substituted pyrroles has been developed via a tandem propargylation/cycloisomerization reaction of α-oxoketene-N,S-acetals with propargyl alcohols. Notably, in the presence of Bronsted acid p-TSA·HO, the reaction afforded the hydrolyzed product propargylated-1,3-dicarbonyl compounds, which upon treatment with CsCO underwent regioselective intramolecular cyclization furnishing tetrasubstituted furan derivatives.
通过α-氧代烯酮-N,S-缩醛与炔丙醇的串联炔丙基化/环异构化反应，开发了一种简便高效的 InCl 催化一锅法合成高度取代的吡咯的方法。值得注意的是，在布朗斯台德酸 p-TSA·HO 的存在下，该反应得到了水解产物炔丙基-1,3-二羰基化合物，后者与 CsCO 反应后进行区域选择性的分子内环化，生成四取代呋喃衍生物。
