Synthesis of isoquinolines via visible light-promoted insertion of vinyl isocyanides with diaryliodonium salts

被引：112

作者：

Jiang, Heng ^{[1
]}

Cheng, Yuanzheng ^{[1
]}

Wang, Ruzhi ^{[1
]}

Zhang, Yan ^{[1
]}

Yu, Shouyun ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Analyt Chem Life Sci, Nanjing 210093, Jiangsu, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 46期

基金：

中国国家自然科学基金;

关键词：

PERIPHERAL BENZODIAZEPINE-RECEPTOR; MEDIATED ELECTROPHILIC CYCLIZATION; H BOND ACTIVATION; DE-NOVO SYNTHESIS; SUBSTITUTED ISOQUINOLINES; PHOTOREDOX CATALYSIS; PHENANTHRIDINE DERIVATIVES; INTERNAL ALKYNES; SULFONYLMETHYL ISOCYANIDES; REGIOSELECTIVE SYNTHESIS;

D O I：

10.1039/c4cc01122h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A synthetic strategy for multi-substituted isoquinoline derivatives has been developed using visible light-promoted vinyl isocyanide insertion with diaryliodonium salts at room temperature. The methodology presented here represents the first example of isoquinoline synthesis via somophilic isocyanide insertion.

引用

收藏

页码：6164 / 6167

页数：4

相关论文

共 56 条

[1] Mapping and fitting the peripheral benzodiazepine receptor binding site by carboxamide derivatives. Comparison of different approaches to quantitative ligand-receptor interaction modeling [J].

Anzini, M ;

Cappelli, A ;

Vomero, S ;

Seeber, M ;

Menziani, MC ;

Langer, T ;

Hagen, B ;

Manzoni, C ;

Bourguignon, JJ .

JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (08) :1134-1150

[2] On the synthesis of vinyl isonitriles [J].

Baldwin, JE ;

Chen, DQ ;

Russell, AT .

CHEMICAL COMMUNICATIONS, 1997, (24) :2389-2390

[3]

Bentley K. W., 1998, The Isoquinoline Alkaloids, V1

[4] Synthesis using aromatic homolytic substitution - recent advances [J].

Bowman, W. Russell ;

Storey, John M. D. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (11) :1803-1822

[5] Mapping the peripheral benzodiazepine receptor binding site by conformationally restrained derivatives of 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide (PK11195) [J].

Cappelli, A ;

Anzini, M ;

Vomero, S ;

DeBenedetti, PG ;

Menziani, MC ;

Giorgi, G ;

Manzoni, C .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (18) :2910-2921

[6] Isocyanide Insertion: De Novo Synthesis of Trifluoromethylated Phenanthridine Derivatives [J].

Cheng, Yuanzheng ;

Jiang, Heng ;

Zhang, Yan ;

Yu, Shouyun .

ORGANIC LETTERS, 2013, 15 (21) :5520-5523

[7] A Pd(II)-Catalyzed Ring-Expansion Reaction of Cyclic 2-Azidoalcohol Derivatives: Synthesis of Azaheterocycles [J].

Chiba, Shunsuke ;

Xu, Yan-Jun ;

Wang, Yi-Feng .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) :12886-+

[8] Ruthenium-Catalyzed Highly Regioselective Cyclization of Ketoximes with Alkynes by C-H Bond Activation: A Practical Route to Synthesize Substituted Isoquinolines [J].

Chinnagolla, Ravi Kiran ;

Pimparkar, Sandeep ;

Jeganmohan, Masilamani .

ORGANIC LETTERS, 2012, 14 (12) :3032-3035

[9]

Dömling A, 2005, SYNTHESIS-STUTTGART, P662

[10] Synthesis of substituted isoquinolines utilizing palladium-catalyzed α-arylation of ketones [J].

Donohoe, Timothy J. ;

Pilgrim, Ben S. ;

Jones, Geraint R. ;

Bassuto, Jose A. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2012, 109 (29) :11605-11608

← 1 2 3 4 5 6 →