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

• Published in: Natural product communications Vol. 10; no. 6; pp. 903 - 912
• Main Authors: Shimada, Kazuaki, Izumi, Hironori, Otashiro, Koki, Noro, Kensuke, Aoyagi, Shigenobu, Takikawa, Yuji, Korenaga, Toshinobu
• Format: Journal Article
• Language: English
• Published: Los Angeles, CA SAGE Publications 01.06.2015
• Subjects: Molecular Structure; Quinolines - chemical synthesis; Quinolines - chemistry; Selenium - chemistry; Sulfur - chemistry; Thiones - chemistry; α, β-Unsaturated selenoamide; α, β-Unsaturated thioamide; Propargyl methyl ether; Quinoline-2(1 H)-selone; Quinoline-2(1 H)-thione
• ISSN: 1934-578X; 1555-9475
• DOI: 10.1177/1934578X1501000628

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.