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

共 61 条

[51] Cu(I)-catalyzed direct addition and asymmetric addition of terminal alkynes to imines
Wei, CM
Mague, JT
Li, CJ
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (16) : 5749 - 5754
[52] A highly efficient three-component coupling of aldehyde, alkyne, and amines via C-H activation catalyzed by gold in water
Wei, CM
Li, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) : 9584 - 9585
[53] The first silver-catalyzed three-component coupling of aldehyde, alkyne, and amine
Wei, CM
Li, ZG
Li, CJ
[J]. ORGANIC LETTERS, 2003, 5 (23) : 4473 - 4475
[54] Enantioselective direct-addition of terminal alkynes to imines catalyzed by copper(I)pybox complex in water and in toluene
Wei, CM
Li, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (20) : 5638 - 5639
[55] Transition metal salt-catalyzed direct three-component Mannich reactions of aldehydes, ketones, and carbamates:: Efficient synthesis of N-protected β-aryl-β-amino ketone compounds
Xu, LW
Xia, CG
Li, L
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (24) : 8482 - 8484
[56] Yamada K, 1999, ANGEW CHEM INT EDIT, V38, P3504, DOI 10.1002/(SICI)1521-3773(19991203)38:23<3504::AID-ANIE3504>3.0.CO
[57] 2-E
[58] Yamada K., 1999, ANGEW CHEM, V111, P3713, DOI [10.1002/(SICI)1521-3757(19991203)111:233.0.CO
[59] 2-Z, DOI 10.1002/(SICI)1521-3757(19991203)111:233.0.CO
[60] 2-Z]

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