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

[1] Improved Method for Preparation of 3-(1H-Indol-3-yl)benzofuran-2(3H)-ones [J].

Grishin, Igor Yu ;

Arutiunov, Nikolai A. ;

Aksenov, Dmitrii A. ;

Aksenov, Nicolai A. ;

Aksenov, Alexander, V ;

Gasanova, Amina Z. ;

Sorokina, Elena A. ;

Lower, Carolyn ;

Rubin, Michael .

MOLECULES, 2022, 27 (06)

[2] Synthesis of 3-[2-(1,3-butadienyl)]-1H-indoles en route to murrapanine analogue [J].

Chakraborty, Amrita ;

Sinha, Surajit .

TETRAHEDRON LETTERS, 2011, 52 (49) :6635-6638

[3] Synthesis of 2-(1H-Indol-2-yl)acetamides via Bronsted Acid-Assisted Cyclization Cascade [J].

Aksenov, Nicolai A. ;

Aksenov, Dmitrii A. ;

Skomorokhov, Anton A. ;

Prityko, Lidiya A. ;

Aksenov, Alexander V. ;

Griaznov, Georgii D. ;

Rubin, Michael .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (19) :12128-12146

[4] Synthesis and Antitumor Activity of 3-(2-Phenyl-1,3-thiazol-4-yl)-1H-indoles and 3-(2-Phenyl-1,3-thiazol-4-yl)-1H-7-azaindoles [J].

Diana, Patrizia ;

Carbone, Anna ;

Barraja, Paola ;

Montalbano, Alessandra ;

Parrino, Barbara ;

Lopergolo, Alessia ;

Pennati, Marzia ;

Zaffaroni, Nadia ;

Cirrincione, Girolamo .

CHEMMEDCHEM, 2011, 6 (07) :1300-1309

[5] Microwave synthesis of 2-[(E)-2-(1H-indol-3-yl)vinyl] hetarenes [J].

Aksenov, Alexander V. ;

Nadein, Oleg N. ;

Aksenov, Nicolai A. ;

Skomorokhov, Anton A. ;

Aksenova, Inna V. ;

Rubin, Michael A. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (10) :865-868

[6] Ethyl 3-[2-(3,4-dimethoxybenzyl)-1-phenylsulfonyl-1H-indol-3-yl]acrylate chloroform hemisolvate [J].

Thenmozhi, M. ;

Kavitha, T. ;

Dhayalan, V. ;

Mohanakrishnan, A. K. ;

Ponnuswamy, M. N. .

ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 :O1460-U1087

[7] Modification of the Gewald methodology for the synthesis of 3-amino-2-(1H-1,2,3-benzotriazol-1-yl) substituted benzofurans, benzothiophenes and 1H-indoles [J].

Rádl, S ;

Obadalova, I .

ARKIVOC, 2005, :4-11

[8] One-Step Synthesis of 2-Amino-5H-pyrimido[5,4-b]indoles, Substituted 2-(1,3,5-triazin-2-yl)-1H-indoles, and 1,3,5-Triazines from Aldehydes [J].

Biswas, Subhasish ;

Batra, Sanjay .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (18) :3492-3499

[9] Automated Multistep Continuous Flow Synthesis of 2-(1H-Indol-3-yl)thiazole Derivatives [J].

Pagano, Nicholas ;

Heil, Marintha L. ;

Cosford, Nicholas D. P. .

SYNTHESIS-STUTTGART, 2012, 44 (16) :2537-2546

[10] Synthesis of 6H-Isoindolo[2,1-a]indol-6-ones via Palladium-Catalyzed Carbonylative Cyclization of 2-(2-Bromophenyl)-1H-indoles [J].

Yoo, Jae Myeong ;

Ho, Son Long ;

Cho, Chan Sik .

SYNLETT, 2016, 27 (09) :1383-1386

← 1 2 3 4 5 →