Direct Conversion of 3-(2-Nitroethyl)-1H-Indoles into 2-(1H-Indol-2-yl)Acetonitriles

被引：9

作者：

Aksenov, Alexander, V ^{[1
]}

Aksenov, Nicolai A. ^{[1
]}

Aleksandrova, Elena, V ^{[1
]}

Aksenov, Dmitrii A. ^{[1
]}

Grishin, Igor Yu ^{[1
]}

Sorokina, Elena A. ^{[2
]}

Wenger, Allison ^{[3
]}

Rubin, Michael ^{[1
,3
]}

机构：

[1] North Caucasus Fed Univ, Dept Chem, 1a Pushkin St, Stavropol 355017, Russia

[2] Peoples Friendship Univ Russia, Organ Chem Dept, RUDN Univ, 6 Miklukho Maklaya St, Moscow 117198, Russia

[3] Univ Kansas, Dept Chem, 1567 Irving Hill Rd, Lawrence, KS 66045 USA

来源：

MOLECULES | 2021年 / 26卷 / 20期

基金：

俄罗斯科学基金会;

关键词：

nitroalkanes; heterocycles; 1,2-alkyl shift; rearrangements; cascade transformations; PRIMARY NITRO-COMPOUNDS; BISINDOLE ALKALOIDS; TRANSFORMATION; CONFIGURATION; NITRILES; INDOLES;

D O I：

10.3390/molecules26206132

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The recently discovered [4+1]-spirocyclization of nitroalkenes to indoles provided a convenient new approach to 2-(1H-indol-2-yl)acetonitriles. However, this reaction was complicated by the formation of inert 3-(2-nitroethyl)-1H-indole byproducts. Herein, we offer a workaround this problem that allows for effective transformation of the unwanted byproducts into acetonitrile target molecules.

引用

页数：16

共 50 条

[21] 2-[(3,5-Diamino-1H-pyrazol-4-yl)methylidene]-1,2-dihydro-3H-indol-3-ones: synthesis and properties [J].

Masterova, N. S. ;

Ryabova, S. Yu. ;

Alekseeva, L. M. ;

Shashkov, A. S. ;

Chernyshev, V. V. ;

Granik, V. G. .

RUSSIAN CHEMICAL BULLETIN, 2009, 58 (09) :1973-1980

[22] 1-[(Imidazolidin-2-yl)imino]-1H-indoles as new hypotensive agents: synthesis and in vitro and in vivo biological studies [J].

Kornicka, Anita ;

Wasilewska, Aleksandra ;

Saczewski, Jaroslaw ;

Hudson, Alan L. ;

Boblewski, Konrad ;

Lehmann, Artur ;

Gzella, Karol ;

Belka, Mariusz ;

Saczewski, Franciszek ;

Gdaniec, Maria ;

Rybczynska, Apolonia ;

Baczek, Tomasz .

CHEMICAL BIOLOGY & DRUG DESIGN, 2017, 89 (03) :400-410

[23] Synthesis and X-ray Structure Determination of Some New 5-(Pyrazol-3-yl)-1H-indoles using 5-(1H-Indol-3-yl)-1-phenyl-1H-pyrazole-3-carbohydrazide as a Precursor [J].

Baashen, Mohammed A. .

INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 29 (01) :93-97

[24] (1H-Benzo[d][1,2,3] triazol-1-yl)(5-bromo-1-hydroxy-1H-indol-3yl) methanone [J].

Tibiletti, Francesco ;

Penoni, Andrea ;

Palmisano, Giovanni ;

Maspero, Angelo ;

Nicholas, Kenneth M. ;

Vaghi, Luca .

MOLBANK, 2014, (03)

[25] The crystal structure of 3-(6-fluoro-1H-indol-3-yl)-1-methylquinoxalin-2(1H)-one, C17H12FN3O [J].

Ni, Hang-Cheng ;

Zhao, Min ;

Li, Wen-An ;

Liu, Zhen-Xiang ;

Shao, Ling-Li ;

Chen, Miao-Miao .

ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2024, 239 (05) :923-925

[26] A novel and convenient route for the construction of 5-((1H-1,2,4-triazol-1-yl)methyl)-1H-indoles and its application in the synthesis of Rizatriptan [J].

He, Yi ;

Li, Xiaolong ;

Li, Jue ;

Li, Xiaocen ;

Guo, Li ;

Hai, Li ;

Wu, Yong .

TETRAHEDRON LETTERS, 2014, 55 (29) :3938-3941

[27] Pd-Catalyzed One-Pot Two-Step Synthesis of 2-(1H-indol-3-yl)-2-phenylindolin-3-ones from 2-Alkynyl Arylazides and Indoles [J].

Yong, Wanxiong ;

Li, Ping ;

Sheng, Rong ;

Rao, Weidong ;

Zhang, Xiaoxiang .

CHEMISTRYSELECT, 2018, 3 (41) :11696-11699

[28] A Facile Synthesis of Novel (Z)-ethyl-3-(5-substituted-1-alkyl/aryl-1H-indol-3-yl)-2-(1H-tetrazol-5-yl)acrylate [J].

Bakkolla, Mahesh Goud ;

Taduri, Ashok Kumar ;

Bhoomireddy, Rama Devi .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (01) :92-98

[29] One-Pot Copper-Catalyzed Cascade Bicyclization Strategy for Synthesis of 2-(1H-Indol-1-yl)-4,5-dihydrothiazoles and 2-(1H-Indol-1-yl)thiazol-5-yl Aryl Ketones with Molecular Oxygen as an Oxygen Source [J].

Xie, Jialin ;

Guo, Zhonglin ;

Huang, Yuanqiong ;

Qu, Yi ;

Song, Hongjian ;

Song, Haibin ;

Liu, Yuxiu ;

Wang, Qingmin .

ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (03) :490-495

[30] Copper-catalyzed oxidative trimerization of indoles by using TEMPO to construct quaternary carbon centers: the synthesis of 2-(1H-indol-3-yl)-2,3′-biindolin-3-ones [J].

Kong, Yu-Bo ;

Zhu, Jia-Yi ;

Chen, Zheng-Wang ;

Liu, Liang-Xian .

CANADIAN JOURNAL OF CHEMISTRY, 2014, 92 (04) :269-273

← 1 2 3 4 5 →