Department of Chemistry and Center of Excellence for Innovation in Chemistry (PERCH-CIC), Faculty of Science , Mahidol University , Rama 6 Road , Bangkok 10400 , Thailand.
J Org Chem. 2019 Dec 6;84(23):15131-15144. doi: 10.1021/acs.joc.9b02081. Epub 2019 Nov 14.
A new synthetic approach for the synthesis of indolo[2,3-]quinolines and benzothieno[2,3-]quinolines has been developed by employing the freshly prepared -alkynylisocyanobenzenes derived from -alkynylformamide derivatives as substrates. The synthetic transformations involved chloride-ion-triggered 6- cyclization of -alkynylisocyanobenzenes to generate 2-chloroquinolines in situ, which further cyclized intramolecularly with nitrogen or sulfur atom via a cascade process to provide the corresponding indolo[2,3-]quinolines and benzothieno[2,3-]quinolines, respectively, in moderate to excellent yields.
一种新的合成吲哚并[2,3-]喹啉和苯并噻吩并[2,3-]喹啉的方法已经开发出来，该方法采用新鲜制备的-炔基异氰基苯衍生物作为底物。这些合成转化涉及氯离子触发的-炔基异氰基苯的 6-环化反应，原位生成 2-氯喹啉，然后通过级联反应与氮或硫原子分子内环化，分别以中等至优异的收率得到相应的吲哚并[2,3-]喹啉和苯并噻吩并[2,3-]喹啉。
