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] Synthesis and biological evaluation of 3-(azolylmethyl)-1H-indoles and 3-(α-azolylbenzyl)-1H-indoles as selective aromatase inhibitors
Le Borgne, Marc
Marchand, Pascal
Nourrisson, Marie-Renee
Loquet, Denis
Palzer, Martina
Le Baut, Guillaume
Hartmann, Rolf W.
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2007, 22 (05) : 667 - 676
[22] Synthesis of 2-(1H-Indol-2-yl)acetamides via Bronsted Acid-Assisted Cyclization Cascade
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
[23] Cardiotoxic effects of [3-[2-(diethylamino)ethyl]-1H-indol-4-yl] acetate and 3-[2-[ethyl(methyl)amino]ethyl]-1H-indol-4-ol
Yoon, Kyung Sik
Lee, Jin-Moo
Kim, Young-Hoon
Suh, Soo Kyung
Cha, Hye Jin
TOXICOLOGY LETTERS, 2020, 319 : 40 - 48
[24] 2′-[(5-bromo-1H-indol-3-yl)methylene]-2-(1H-indol-3-yl)acetohydrazide ethyl acetate solvate
Ali, Hapipah M.
Shimar, Jamaludin Nazzatush
Ng, Seik Weng
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O2731 - U1620
[25] Dichloridobis(2-{1-[2-(1H-indol-3-yl)-ethyliminio]ethyl}phenolate-κO)zinc(II)-2-{1-[2-(1H-indol-3-yl)ethyliminio]ethyl}-phenolate (1/2)
Ali, Hapipah M.
Ibrahim, Mohamed
Mustafa, Mohamed
Rizal, Mohd. Razali
Ng, Seik Weng
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : M718 - U923
[26] An entry to 2-(cyclobut-1-en-1-yl)-1H-indoles through a cyclobutenylation/deprotection cascade
Natho, Philipp
Yang, Zeyu
Allen, Lewis A. T.
Rey, Juliette
White, Andrew J. P.
Parsons, Philip J.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (18) : 4048 - 4053
[27] Synthesis of annulated bis-indoles through Au(I)/Bronsted acid-catalyzed reactions of (1H-indol-3-yl)(aryl)methanols with 2-(arylethynyl)-1H-indoles
Inamdar, Suleman M.
Gonnade, Rajesh G.
Patil, Nitin T.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (04) : 863 - 869
[28] (Z)-3-(1H-indol-3-yl)-2-(3-thienyl)acrylonitrile and (Z)-3-[1-(4-tert-butylbenzyl)-1H-indol-3-yl]2-(3-thienyl)acrylonitrile
Sonar, VN
Parkin, S
Crooks, PA
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2005, 61 : O78 - O80
[29] (Z)-3-(1H-indol-3-yl)-2-(4-nitrophenyl)acrylonitrile
Qian, Bao-Hua
Liu, Wei-Wei
Hu, Hong-Wen
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O3627 - U4615
[30] Quantum chemical and third order nonlinear optical investigation of (E)-1-(1H-imidazol-1-yl)-3-(1H-indol-2-yl)prop-2-en-1-one
Arjunan, G.
Karunathan, R.
Muhamed, R. Raj
Sathyanarayanamoorthi, V
INDIAN JOURNAL OF CHEMISTRY, 2023, 62 (08): : 808 - 815

← 1 2 3 4 5 →