Department of Chemistry, Zhejiang University , Hangzhou 310027, P. R. China.
Org Lett. 2013 Nov 15;15(22):5894-7. doi: 10.1021/ol402996x. Epub 2013 Nov 5.
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.
通过铜催化的炔叠氮环加成（CuAAC）、Dimroth 重排、1,5-OR 迁移/1,5-H 迁移和 6π-电环化环闭（6π-ERC）的级联过程，从邻炔基苯乙缩醛和磺酰基叠氮化物高效合成 1,3-/1,1-二烷氧基 1,2-二氢异喹啉。还公开了将生成的 1,3-二烷氧基-1,2-二氢异喹啉扩展到异喹啉鎓盐。
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