Construction of Isoquinolin-1(2H)-ones by Copper-Catalyzed Tandem Reactions of 2-(1-Alkynyl)benzaldimines with Water

被引：26

作者：

Zhang, Mingliang ^{[1
]}

Zhang, Hui-Jun ^{[1
]}

Ruan, Wenqing ^{[1
]}

Wen, Ting-Bin ^{[1
]}

机构：

[1] Xiamen Univ, Coll Chem & Chem Engn, Dept Chem, Xiamen 361005, Fujian, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 27期

基金：

中国国家自然科学基金;

关键词：

Homogeneous catalysis; Copper; Cyclization; Oxidation; Tandem reaction; Nitrogen heterocycles; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; CONCISE SYNTHESIS; SUBSTITUTED; 3-METHYLENEISOINDOLIN-1-ONES; 3,4-DISUBSTITUTED ISOQUINOLINES; INTRAMOLECULAR CYCLIZATION; ELECTROPHILIC CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; NUCLEOPHILIC-ADDITION; BIOLOGICAL EVALUATION;

D O I：

10.1002/ejoc.201500908

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Cu(OAc)(2)-catalyzed tandem reaction of 2-(1-alkynyl)-benzaldimines with water for the synthesis of isoquinolin1-(2H)-ones was developed. Moreover, 4-halogen-substituted isoquinolin-1(2H)-ones were obtained in good yields simply by including N-halosuccinimides (NXS: X = Cl, Br, I) in the reaction system. Mechanistic studies indicated that the reactions are probably initiated by highly regioselective intramolecular cyclization of 2-(1-alkynyl) benzaldimines to give the corresponding isoquinolinium intermediates.

引用

页码：5914 / 5918

页数：5

共 71 条

[21] Rh2(OAc)4-AgOTf Cooperative Catalysis in Cyclization/Three-Component Reactions for Concise Synthesis of 1,2-Dihydroisoquinolines
Guo, Zhenqiu
Cai, Mei
Jiang, Jun
Yang, Liping
Hu, Wenhao
[J]. ORGANIC LETTERS, 2010, 12 (04) : 652 - 655
[22] Palladium-catalyzed oxidative activation of arylcyclopropanes
He, Zhi
Yudin, Andrei K.
[J]. ORGANIC LETTERS, 2006, 8 (25) : 5829 - 5832
[23] Microwave assisted copper-free Sonogashira coupling/5-exo-dig cycloisomerization domino reaction: access to 3-(phenylmethylene)isoindolin-1-ones and related heterocycles
Hellal, Malik
Cuny, Gregory D.
[J]. TETRAHEDRON LETTERS, 2011, 52 (42) : 5508 - 5511
[24] Synthesis of isoquinolines by palladium-catalyzed cyclization, followed by a Heck reaction
Huang, QH
Larock, RC
[J]. TETRAHEDRON LETTERS, 2002, 43 (19) : 3557 - 3560
[25] Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes
Huang, QH
Hunter, JA
Larock, RC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) : 3437 - 3444
[26] Synthesis of isoquinolines and naphthyridines by electrophilic ring closure of iminoalkynes
Huang, QH
Hunter, JA
Larock, RC
[J]. ORGANIC LETTERS, 2001, 3 (19) : 2973 - 2976
[27] Synthesis of 4-(1-alkenyl)isoquinolines by palladium(II)-catalyzed cyclization/olefination
Huang, QH
Larock, RC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) : 980 - 988
[28] A SHORT SYNTHESIS OF (+)-LYCORICIDINE
HUDLICKY, T
OLIVO, HF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) : 9694 - 9696
[29] Copper(II)Chloride-Mediated Cyclization Reaction of N-Alkoxy-ortho-alkynylbenzamides
Jithunsa, Manita
Ueda, Masafumi
Miyata, Okiko
[J]. ORGANIC LETTERS, 2011, 13 (03) : 518 - 521
[30] Nickel-catalyzed decarbonylative addition of phthalimides to alkynes
Kajita, Yuichi
Matsubara, Seijiro
Kurahashi, Takuya
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (19) : 6058 - +

← 1 2 3 4 5 6 7 8 →