1217436-33-3Relevant academic research and scientific papers
Regioselective synthesis of 3-bromoquinoline derivatives and diastereoselective synthesis of tetrahydroquinolines via acid-promoted rearrangement of arylmethyl azides
Tummatorn, Jumreang,Poonsilp, Piyapratch,Nimnual, Phongprapan,Janprasit, Jindaporn,Thongsornkleeb, Charnsak,Ruchirawat, Somsak
, p. 4516 - 4525 (2015/05/13)
Regioselective synthesis of 3-bromoquinoline derivatives was achieved via a formal [4 + 2]-cycloaddition between N-aryliminium ion, generated from arylmethyl azides, and 1-bromoalkynes. This method could also be applied to other quinoline derivatives using appropriate alkynes. Moreover, the current strategy could be utilized for the diastereoselective synthesis of tetrahydroquinoline derivatives employing alkenyl substrates in good to excellent yields.
Synthesis of substituted quinolines by the electrophilic cyclization of n-(2-alkynyl)anilines
Zhang, Xiaoxia,Yao, Tuanli,Campo, Marino A.,Larock, Richard C.
supporting information; experimental part, p. 1177 - 1187 (2010/04/02)
A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I2, Br2, PhSeBr, and p-O2NC6H4SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the 3-position have been synthesized by the Hg(OTf)2-catalyzed ring closure of these same alkynylanilines.
