A Synthesis of 3,4-Dihydroisoquinolin-1(2H)-one via the Rhodium-Catalyzed Alkylation of Aromatic Amides with N-Vinylphthalimide

被引：26

作者：

He, Qiyuan ^{[1
]}

Chatani, Naoto ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 21期

关键词：

H BOND ACTIVATION; BIDENTATE DIRECTING GROUPS; RH(I)-CATALYZED ALKYLATION; ALKENES; CONSTRUCTION; DERIVATIVES; ANTAGONISTS; GENERATION; REACTIVITY; OXIDATION;

D O I：

10.1021/acs.joc.8b02249

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The alkylation of C-H bonds with N-vinylphthalimide by a rhodium-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety as the directing group is reported. N-Vinylphthalimide functions as a 2-aminoethylating reagent. The resulting alkylated products can be converted into 3,4-dihydroisoquinolin-1(2H)-one derivatives in a one-pot transformation. Deuterium-labeling experiments suggest that the reaction proceeds through a carbene mechanism.

引用

页码：13587 / 13594

页数：8

共 43 条

[1] A REVISION OF THE STRUCTURE OF THE ISOQUINOLONE ALKALOID THALFLAVINE [J].

ALY, Y ;

GALAL, A ;

WONG, LK ;

FU, EW ;

LIN, FT ;

DUAH, FK ;

SCHIFF, PL .

PHYTOCHEMISTRY, 1989, 28 (07) :1967-1971

[2] Rhodium and Iridium Complexes of Bulky Tertiary Phosphine Ligands. Searching for Isolable Cationic MIII Alkylidenes [J].

Campos, Jesus ;

Carmona, Ernesto .

ORGANOMETALLICS, 2015, 34 (11) :2212-2221

[3] Nickel Catalysts/N,N′-Bidentate Directing Groups: An Excellent Partnership in Directed C-H Activation Reactions [J].

Castro, Luis C. Misal ;

Chatani, Naoto .

CHEMISTRY LETTERS, 2015, 44 (04) :410-421

[4] The Use of a Rhodium Catalyst/8-Aminoquinoline Directing Group in the C-H Alkylation of Aromatic Amides with Alkenes: Possible Generation of a Carbene Intermediate from an Alkene [J].

Chatani, Naoto .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2018, 91 (02) :211-222

[5] Recyclable NaHSO4 catalyzed alkylation of tert-enamides with indoles or amines in water: facile construction of pharmaceutically analogous bis-alkaloid scaffolds [J].

Chu, Xue-Qiang ;

Wang, Shun-Yi ;

Ji, Shun-Jun .

RSC ADVANCES, 2013, 3 (22) :8380-8387

[6] Branch Selective Mural-type Alkene Hydroarylation Reactions [J].

Crisenza, Giacomo E. M. ;

Bower, John F. .

CHEMISTRY LETTERS, 2016, 45 (01) :2-9

[7] Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon-Hydrogen Bonds [J].

Daugulis, Olafs ;

Roane, James ;

Tran, Ly Dieu .

ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) :1053-1064

[8] Palladium- and Copper-Catalyzed Arylation of Carbon-Hydrogen Bonds [J].

Daugulis, Olafs ;

Do, Hien-Quang ;

Shabashov, Dmitry .

ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (08) :1074-1086

[9] Transition-Metal-Catalyzed C-H Alkylation Using Alkenes [J].

Dong, Zhe ;

Ren, Zhi ;

Thompson, Samuel J. ;

Xu, Yan ;

Dong, Guangbin .

CHEMICAL REVIEWS, 2017, 117 (13) :9333-9403

[10] ANTIVIRAL (RNA) ACTIVITY OF SELECTED AMARYLLIDACEAE ISOQUINOLINE CONSTITUENTS AND SYNTHESIS OF RELATED SUBSTANCES [J].

GABRIELSEN, B ;

MONATH, TP ;

HUGGINS, JW ;

KEFAUVER, DF ;

PETTIT, GR ;

GROSZEK, G ;

HOLLINGSHEAD, M ;

KIRSI, JJ ;

SHANNON, WM ;

SCHUBERT, EM ;

DARE, J ;

UGARKAR, B ;

USSERY, MA ;

PHELAN, MJ .

JOURNAL OF NATURAL PRODUCTS, 1992, 55 (11) :1569-1581

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