69248-58-4Relevant articles and documents
Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses
Hwu, Jih Ru,Panja, Avijit,Gupta, Nitesh K.,Hu, Yu-Chen,Tan, Kui-Thong,Lin, Chun-Cheng,Hwang, Kuo-Chu,Hsu, Ming-Hua,Huang, Wen-Chieh,Tsay, Shwu-Chen
, p. 683 - 693 (2021/01/18)
Synthetic application of arynes is broadened by their reactions with neutral N-, S-, and O-containing nucleophiles to produce three types of compounds. Accordingly, 1,2-dihydroquinolines are synthesized from Schiff bases, alkynes, and arynes through a Diels-Alder reaction. Epoxides are prepared from thioethers and arynes along with aldehydes or ketones through a Johnson-Corey-Chaykovsky reaction. Phenolic ethers are produced from allyl ethers and arynes through a Claisen-type rearrangement. These target molecules, including natural products γ-asarone, asaricin, and a cholesteryl phenolic ether, are formed through reactions initiated by arynes. These new reactions share a prevailing feature of domino processes, which are carried out in a single flask and afford the desired products in good to high yields.