Pd-Catalyzed Sequential Arylation of 7-Azaindoles: Aggregate-Induced Emission of Tetra-Aryl 7-Azaindoles

被引：19

作者：

Cardoza, Savio ^{[1
]}

Das, Parthasarathi ^{[2
]}

Tandon, Vibha ^{[1
]}

机构：

[1] Jawaharlal Nehru Univ, Special Ctr Mol Med, New Delhi 110067, India

[2] Indian Inst Technol, Indian Sch Mines, Dept Chem, Dhanbad 826004, Jharkhand, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 21期

关键词：

C-H ARYLATION; STATE PROTON-TRANSFER; DIRECT C-2 ARYLATION; PHOTOPHYSICAL PROPERTIES; INDOLES; DERIVATIVES; PYRROLES; ACCESS; SUBSTITUENTS; ALKYNYLATION;

D O I：

10.1021/acs.joc.9b02187

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pd-catalyzed synthesis of multi-aryl 7-azaindoles using sequential arylation of 5-bromo-6-chloro-3-iodo-1-methyl-1H-pyrrolo[2,3-b] pyridine is established. Four diverse aryl groups are installed in a chemo-selective fashion providing a general method to synthesize sterically encumbered compounds and extended 7-azaindoles in 48-95% yields. Three-selective sequential arylations at C-3, C-5, and C-6 via Suzuki-Miyaura cross-coupling followed by direct C-2 arylation using a Pd catalyst and AgOTf as an additive are highlights of the present work. Interestingly, the tetra-aryl 7-azaindoles showed aggregate-induced emission (AIE) making it potentially useful as fluorophores in OLEDs, sensors, and bio-imaging tools.

引用

收藏

页码：14015 / 14029

页数：15

相关论文

共 86 条

[51] Programmed synthesis of triarylnitroimidazoles via sequential cross-coupling reactions [J].

Raina, Gaurav ;

Kannaboina, Prakash ;

Mupparapu, Nagaraju ;

Raina, Sushil ;

Ahmed, Qazi Naveed ;

Das, Parthasarathi .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (08) :2134-2147

[52] The developability of heteroaromatic and heteroaliphatic rings - do some have a better pedigree as potential drug molecules than others? [J].

Ritchie, Timothy J. ;

Macdonald, Simon J. F. ;

Peace, Simon ;

Pickett, Stephen D. ;

Luscombe, Christopher N. .

MEDCHEMCOMM, 2012, 3 (09) :1062-1069

[53] Transition Metal-Catalyzed C-H Activation of Indoles [J].

Sandtorv, Alexander H. .

ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (11) :2403-2435

[54] Improved Synthesis of the Selective Rho-Kinase Inhibitor 6-Chloro-N4-{3,5-difluoro-4-[(3-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)oxy]phenyl}pyrimidin-2,4-diamine [J].

Schirok, Hartmut ;

Paulsen, Holger ;

Kroh, Walter ;

Chen, Gang ;

Gao, Ping .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2010, 14 (01) :168-173

[55] SYNTHESIS OF 4-AMINO-1H-PYRROLO[2,3-B]PYRIDINE (1,7-DIDEAZAADENINE) AND 1H-PYRROLO[2,3-B]PYRIDINE-4-OL (1,7-DIDEAZAHYPOXANTHINE) [J].

SCHNELLER, SW ;

LUO, JK .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (20) :4045-4048

[56] Direct transition metal-catalyzed functionalization of heteroaromatic compounds [J].

Seregin, Ilya V. ;

Gevorgyan, Vladimir .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1173-1193

[57] Photophysics and biological applications of 7-azaindole and its analogs [J].

Smirnov, AV ;

English, DS ;

Rich, RL ;

Lane, J ;

Teyton, L ;

Schwabacher, AW ;

Luo, S ;

Thornburg, RW ;

Petrich, JW .

JOURNAL OF PHYSICAL CHEMISTRY B, 1997, 101 (15) :2758-2769

[58] Metal-Catalyzed Cross-Coupling Reactions on Azaindole Synthesis and Functionalization [J].

Sofia Santos, A. ;

Mortinho, Ana C. ;

Marques, M. Manuel B. .

MOLECULES, 2018, 23 (10)

[59] Ru-Catalysed C-H Arylation of Indoles and Pyrroles with Boronic Acids: Scope and Mechanistic Studies [J].

Sollert, Carina ;

Devaraj, Karthik ;

Orthaber, Andreas ;

Gates, Paul J. ;

Pilarski, Lukasz T. .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (14) :5380-5386

[60] Discovery, characterization, and lead optimization of 7-azaindole non-nucleoside HIV-1 reverse transcriptase inhibitors [J].

Stanton, Richard A. ;

Lu, Xiao ;

Detorio, Mervi ;

Montero, Catherine ;

Hammond, Emily T. ;

Ehteshami, Maryam ;

Domaoal, Robert A. ;

Nettles, James H. ;

Feraud, Michel ;

Schinazi, Raymond F. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (16) :4101-4105

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