American Chemical Society
ol402996x_si_001.pdf (4.63 MB)

Cu-Catalyzed 1,2-Dihydroisoquinolines Synthesis from o‑Ethynyl Benzacetals and Sulfonyl Azides

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journal contribution
posted on 2013-11-15, 00:00 authored by Lang Sun, Yuanxun Zhu, Ping Lu, Yanguang Wang
An efficient synthesis of 1,3-/1,1-dialkoxy 1,2-dihydroisoquinolines from o-ethynylbenzacetals and sulfonyl azides via a cascade process combining copper-catalyzed alkyne–azide cycloaddition (CuAAC), Dimroth rearrangement, 1,5-OR shift/1,5-H shift, and 6π-electrocyclic ring closure (6π-ERC) is described. Extension of the produced 1,3-dialkoxy-1,2-dihydroisoquinolines to isoquinolium salts is also disclosed.