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Regioselective Synthesis of 3‑Bromoquinoline Derivatives and Diastereoselective Synthesis of Tetrahydroquinolines via Acid-Promoted Rearrangement of Arylmethyl Azides
journal contribution
posted on 2015-05-01, 00:00 authored by Jumreang Tummatorn, Piyapratch Poonsilp, Phongprapan Nimnual, Jindaporn Janprasit, Charnsak Thongsornkleeb, Somsak RuchirawatRegioselective
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.