Transition-Metal-Free Arylation of N-Alkyl-tetrahydroisoquinolines under Oxidative Conditions: A Convenient Synthesis of C1-Arylated Tetrahydroisoquinoline Alkaloids

被引：27

作者：

Singh, Kamal Nain ^{[1
,2
]}

Kessar, Satinder V. ^{[1
,2
]}

Singh, Paramjit ^{[1
,2
]}

Singh, Pushpinder ^{[3
]}

Kaur, Manjot ^{[1
,2
]}

Batra, Aanchal ^{[1
,2
]}

机构：

[1] Panjab Univ, Dept Chem, Chandigarh 160014, India

[2] Panjab Univ, Ctr Adv Studies Chem, Chandigarh 160014, India

[3] DAV Univ, Dept Chem, Jalandhar 144025, India

来源：

SYNTHESIS-STUTTGART | 2014年 / 46卷 / 19期

关键词：

arylation; tetrahydroisoquinoline; C-H activation; alkaloids; metal-free; SP(3) C-H; DEHYDROGENATIVE COUPLING REACTIONS; ONE-POT SYNTHESIS; TERTIARY-AMINES; HIGHLY EFFICIENT; BOND ARYLATION; 1-ARYL-TETRAHYDROISOQUINOLINE ANALOGS; DIRECT FUNCTIONALIZATION; NUCLEOPHILIC-ADDITION; CRYPTOSTYLINE-II;

D O I：

10.1055/s-0034-1378337

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple protocol for the C1 arylation of tetrahydroisoquinolines with aryl Grignard reagents via diethyl azodicarboxylate (DEAD) mediated oxidative C-H activation under metal-free conditions has been developed. The target compounds, including some naturally occurring alkaloids, were obtained in moderate to good yields.

引用

页码：2644 / 2650

页数：7

共 95 条

[61]

Ozturk T., 2000, The Alkaloids: Chemistry and Biology, V53, pg, P120

[62] Oxidative Arylation of Isochroman [J].

Park, Soo J. ;

Price, Jason R. ;

Todd, Matthew H. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (02) :949-955

[63] SYNTHESIS OF SOME ISOQUINOLINE DERIVATIVES RELATED TO PODOPHYLLOTOXIN [J].

REEVE, W ;

EARECKSON, WM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (11) :5195-5197

[64] A one-pot synthesis of (±) cryptostylines I, II, III [J].

Ruchirawat, S ;

Bhavakul, V ;

Chaisupakitsin, M .

SYNTHETIC COMMUNICATIONS, 2003, 33 (04) :621-625

[65] Synthesis of ultra-short-acting neuromuscular blocker GW 0430: A remarkably stereo- and regioselective synthesis of mixed tetrahydroisoquinolinium chlorofumarates [J].

Samano, V ;

Ray, JA ;

Thompson, JB ;

Mook, RA ;

Jung, DK ;

Koble, CS ;

Martin, MT ;

Bigham, EC ;

Regitz, CS ;

Feldman, PL ;

Boros, EE .

ORGANIC LETTERS, 1999, 1 (12) :1993-1996

[66] Biocatalytic Enantioselective Oxidative C-C Coupling by Aerobic C-H Activation [J].

Schrittwieser, Joerg H. ;

Resch, Verena ;

Sattler, Johann H. ;

Lienhart, Wolf-Dieter ;

Durchschein, Katharina ;

Winkler, Andreas ;

Gruber, Karl ;

Macheroux, Peter ;

Kroutil, Wolfgang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) :1068-1071

[67] Bronsted Acid Catalyzed C-H Functionalization of N-Protected Tetrahydroisoquinolines via Intermediate Peroxides [J].

Schweitzer-Chaput, Bertrand ;

Klussmann, Martin .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (04) :666-671

[68] Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics [J].

Scott, JD ;

Williams, RM .

CHEMICAL REVIEWS, 2002, 102 (05) :1669-1730

[69] Catalytic asymmetric Pictet-Spengler reaction [J].

Seayad, J ;

Seayad, AM ;

List, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (04) :1086-1087

[70] pNapuercleophilic Addition of Lewis Acid Complexed α-Amino Carbanions to Arynes: Synthesis of 1-Aryl-N-methyl-1,2,3,4-tetrahydroisoquinolines [J].

Singh, Kamal Nain ;

Singh, Paramjit ;

Sharma, Esha ;

Deol, Yadwinder Singh .

SYNTHESIS-STUTTGART, 2014, 46 (13) :1739-1750

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