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
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
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DOI：
10.1021/jo070615f
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发表时间：
2007-06-08
影响因子：
3.6
通讯作者：
Takemoto, Yoshiji
中科院分区：
文献类型：
--
作者：
Obika, Shingo;Kono, Hideki;Takemoto, Yoshiji
以亲碳刘易斯酸、In（OTf）（3）、NiCl 2和AuCl（PPh 3）/AgNTf 2为催化剂，通过2-（1-炔基）芳醛亚胺的亲核加成和环化反应，合成了1，3-二取代1，2-二氢异喹啉类化合物.在刘易斯酸催化的有机金属试剂串联反应中，质子源如水、CF 3CH 2 OH和2，6-二叔丁基-4-甲氧基苯酚的加入是必不可少的。通过切换这些催化剂，各种类型的亲核试剂，如烯丙基锡烷，甲硅烷基烯醇醚，烯基硼酸，和活性亚甲基化合物，可以在该转化中的1，2-二氢异喹啉的C-1位引入。此外，该方法也适用于2-（1-炔基）芳醛的串联反应合成1H-异色烯衍生物。
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.