One-Pot Synthesis of N-Alkyl Indole from Indoline-2-carboxylic Acids and Alkyl Halides by 2,3-Dicyano-5,6-dichlorobenzoquinone (DDQ) Mediated Oxidative Decaboylative Aromatization

被引：2

作者：

Zhu, Runyu ^{[1
]}

Zhai, Min ^{[1
]}

Liu, Shuang ^{[1
]}

Liu, Xingtong ^{[1
]}

Wang, Zhen ^{[2
]}

Ju, Ruijun ^{[3
]}

Yu, Xinhong ^{[1
]}

机构：

[1] East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Shanghai Key Lab New Drug Design,Minist Educ, State Key Lab Bioengn Reactors,Sch Pharm, Shanghai 200237, Peoples R China

[2] Linyi Univ, Sch Pharm, Linyi 276000, Shandong, Peoples R China

[3] Beijing Inst Petrochem Technol, Coll Chem Engn, Beijing 102617, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 40卷 / 07期

基金：

美国国家科学基金会;

关键词：

aromatization; 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ); decarboxylation; N-alkyl indoles; oxidation; EFFICIENT SYNTHESIS;

D O I：

10.6023/cjoc202001025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of N-alkyl indoles via 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ) mediated intramolecular oxidative decarboxvlative aromatization of N-alkylindoline-2-carboxylic acids is reported. The good compatibility of this process leads to the development of a mild and metal-free one-pot synthesis of N-alkyl indoles from alkyl halides and indoline carboxylic acid. The one-pot three-component synthesis of 1,4-bis((1H-indol-1-yl)methyl)benzene is also disclosed in satisfied yields.

引用

页码：2045 / 2050

页数：6

共 30 条

[1]

[Anonymous], 2005, AM ETHNOL

[2] Selective Ruthenium-Catalyzed N-Alkylation of Indoles by Using Alcohols [J].

Baehn, Sebastian ;

Imm, Sebastian ;

Mevius, Kathleen ;

Neubert, Lorenz ;

Tillack, Annegret ;

Williams, Jonathan M. J. ;

Beller, Matthias .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (12) :3590-3593

[3] Divergent synthesis of isoindolo[2,1-a]indole and indolo[1,2-a]indole through copper-catalysed C- and N-arylations [J].

Barbero, Nekane ;

SanMartin, Raul ;

Dominguez, Esther .

TETRAHEDRON LETTERS, 2009, 50 (18) :2129-2131

[4] The azaallylic anion as a synthon for Pd-catalyzed synthesis of heterocycles:: Domino two- and three-component synthesis of indoles [J].

Barluenga, Jose ;

Jimenez-Aquino, Agustin ;

Valdes, Carlos ;

Aznar, Fernando .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (09) :1529-1532

[5] Modular Synthesis of Indoles from Imines and o-Dihaloarenes or o-Chlorosulfonates by a Pd-Catalyzed Cascade Process [J].

Barluenga, Jose ;

Jimenez-Aquino, Agustin ;

Aznar, Fernando ;

Valdes, Carlos .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :4031-4041

[6] The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids [J].

Bi, Hai-Peng ;

Zhao, Liang ;

Liang, Yong-Min ;

Li, Chao-Jun .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) :792-795

[7] Synthesis and functionalization of Indoles through palladium-catalyzed reactions [J].

Cacchi, S ;

Fabrizi, G .

CHEMICAL REVIEWS, 2005, 105 (07) :2873-2920

[8] Mechanistic evaluation of metal-catalyzed hydrogen-transfer processes: The Shvo catalyst as an example of computational unravelling [J].

Comas-Vives, Aleix ;

Ujaque, Gregori ;

Lledos, Agusti .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2009, 903 (1-3) :123-132

[9] METHODS FOR DRUG DISCOVERY - DEVELOPMENT OF POTENT, SELECTIVE, ORALLY EFFECTIVE CHOLECYSTOKININ ANTAGONISTS [J].

EVANS, BE ;

RITTLE, KE ;

BOCK, MG ;

DIPARDO, RM ;

FREIDINGER, RM ;

WHITTER, WL ;

LUNDELL, GF ;

VEBER, DF ;

ANDERSON, PS ;

CHANG, RSL ;

LOTTI, VJ ;

CERINO, DJ ;

CHEN, TB ;

KLING, PJ ;

KUNKEL, KA ;

SPRINGER, JP ;

HIRSHFIELD, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (12) :2235-2246

[10] Recent developments in indole ring synthesis-methodology and applications [J].

Gribble, GW .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1045-1075

← 1 2 3 →