Concise synthesis of 1,2-dihydroisoquinolines and 1H-isochromenes by carbophilic Lewis acid-catalyzed tandem nucleophilic addition and cyclization of 2-(1-alkynyl)arylaldimines and 2-(1-alkynyl)arylaldehydes

被引:183
作者
Obika, Shingo
Kono, Hideki
Yasui, Yoshizumi
Yanada, Reiko
Takemoto, Yoshiji [1 ]
机构
[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan
[2] Hiroshima Int Univ, Fac Pharmaceut Sci, Hiroshima, Japan
关键词
D O I
10.1021/jo070615f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
By using carbophilic Lewis acids, In(OTf)(3), NiCl2, and AuCl(PPh3)/AgNTf2, a concise and efficient synthesis of 1,3-disubstituted 1,2-dihydroisoquinolines has been achieved via tandem nucleophilic addition and cyclization of 2-(1-alkynyl)arylaldimines. Addition of proton sources such as water, CF3CH2OH, and 2,6-di-tert-butyl-4-methoxyphenol was essential for the Lewis acid-catalyzed tandem reactions with organometallic reagents. By switching these catalysts, various types of nucleophiles such as allylstannanes, silyl enol ethers, alkenylboronic acids, and active methylene compounds could be introduced at the C-1 position of 1,2-dihydroisoquinolines in this transformation. Furthermore, this method proved to be applicable to the synthesis of 1H-isochromene derivatives via the same tandem reaction of 2-(1-alkynyl)arylaldehydes.
引用
收藏
页码:4462 / 4468
页数:7
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