Direct Mannich and nitro-Mannich reactions with non-activated imines:: AgOTf-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines

被引：218

作者：

Asao, N ^{[1
]}

Yudha, S ^{[1
]}

Nogami, T ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 34期

关键词：

imines; Mannich reaction; nitrogen heterocycles; pronucleophiles; synthetic methods;

D O I：

10.1002/anie.200500795

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) A variety of 1,2-dihydroisoquinoline derivatives 3 have been prepared in good to high yields by the AgOTf-catalyzed reaction of ortho-alkynylaryl aldimines 1 with various pronucleophiles 2 (see scheme). Treatment of 1 with a stoichiometric amount of AgOTf followed by protonation with TfOH produced 4, which suggests the formation of an isoquinolinium intermediate in the present direct addition reaction. Tf=trifluoromethanesulfonyl. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5526 / 5528

页数：3