A Novel One-step Synthesis of Quinoline-2(1H)-thiones and Selones by Treating 3-Aryl-3-(2-aminophenyl)-1-propyn-3-ols with a Base and Elemental Sulfur or Selenium

作者：Shimada Kazuaki^*; Izumi Hironori; Otashiro Koki; Noro Kensuke; Aoyagi Shigenobu; Takikawa Yuji; Korenaga Toshinobu

来源：Natural Product Communications, 2015, 10(6): 903-912.

DOI：10.1177/1934578x1501000628

• Propargyl methyl ether
• alpha,beta-Unsaturated thioamide
• alpha,beta-Unsaturated selenoamide
• Quinoline-2(1H)-thione
• Quinoline-2(1H)-selone

A one-step conversion of 3-aryl-3-(2-aminophenyl)-1-propyn-3-ols into quinoline-2(1H)-thiones and quinoline-2(1H)-selones was achieved only by treating the substrates with n-butyllithium and either elemental sulfur or selenium, respectively. The reactions were assumed to proceed-through an intramolecular nucleophilic attack of the neighboring amino group to the plausible in situ generated reactive species related to chalcogenoketenes. The subsequent mCPBA oxidation of quinoline-2(1H)-selones afforded quinolin-2(1H)-ones in high yields.

• 出版日期2015-6