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

[11] Synthesis and in vitro antifungal evaluation of 2-(2,4-difluorophenyl)-1-[(1H-indol-3-ylmethyl)methylamino]-3-(1H-1,2,4-triazol-1-yl)propan-2-ols
Guillon, Remi
Loge, Cedric
Pagniez, Fabrice
Ferchaud-Roucher, Veronique
Duflos, Muriel
Picot, Carine
Le Pape, Patrice
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2011, 26 (02) : 261 - 269
[12] A 'Click' Approach to the Synthesis of 3-[2-(1-Alkyltriazol-4-yl)ethyl]indoles
Petrini, Marino
Shaikh, Rafik R.
SYNTHESIS-STUTTGART, 2009, (18): : 3143 - 3149
[13] Efficient and general synthesis of oxazino[4,3-a]indoles by cascade addition-cyclization reactions of (1H-indol-2-yl)methanols and vinyl sulfonium salts
An, Jing
Chang, Ning-Jie
Song, Li-Dong
Jin, Yu-Qin
Ma, Ying
Chen, Jia-Rong
Xiao, Wen-Jing
CHEMICAL COMMUNICATIONS, 2011, 47 (06) : 1869 - 1871
[14] A novel synthesis of (E)-1-(2-hydroxyphenyl)-3-(1H-indol-3-yl)-prop-2-en-1-ones from chromone-3-carboxylic acid and indoles
Kornev, Mikhail Yu.
Moshkin, Vladimir S.
Sosnovskikh, Vyacheslav Ya.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2015, 51 (09) : 858 - 860
[15] 3-[4-(1H-Indol-3-yl)-1,3-thiazol-2-yl]-1H-pyrrolo[2,3-b]pyridines, Nortopsentin Analogues with Antiproliferative Activity
Parrino, Barbara
Carbone, Anna
Di Vita, Gloria
Ciancimino, Cristina
Attanzio, Alessandro
Spano, Virginia
Montalbano, Alessandra
Barraja, Paola
Tesoriere, Luisa
Livrea, Maria Antonia
Diana, Patrizia
Cirrincione, Girolamo
MARINE DRUGS, 2015, 13 (04): : 1901 - 1924
[16] Synthesis of 4,6-disubstituted-2-(1H-indol-3-yl)-benzothiazoles
Záletová, J
Dzurilla, M
Kutschy, P
Pazdera, P
Kovácik, V
Aldölfi, J
Bekesová, S
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2004, 69 (02) : 453 - 460
[17] Synthesis and antimicrobial screening of 2-methyl-3-[5-substituted phenyl-1,3,4-oxadiazol-2-yl]-1H-indoles
Bhaskar, V. H.
Subramaniyam, S.
Thakor, R. S.
Jayakar, B.
ASIAN JOURNAL OF CHEMISTRY, 2007, 19 (06) : 4758 - 4762
[18] Efficient synthesis and solid state analysis of 3-(1H-pyrrol-2-yl)quinoxalin-2(1H)-one and 2-(1H-pyrrol-2-yl)-1H-benzo[d]imidazole from pyrrolo-2-ylglyoxyl acid
Szydlo, Florence
Andrioletti, Bruno
Rose, Eric
Duhayon, Carine
TETRAHEDRON LETTERS, 2008, 49 (23) : 3749 - 3751
[19] 2-[(3,5-Diamino-1H-pyrazol-4-yl)methylidene]-1,2-dihydro-3H-indol-3-ones: synthesis and properties
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
[20] Simple, novel, and efficient synthesis of ethyl 2-(2-(1H-indol-3-yl)benzo[d]thiazol-3(2H)-yl)-2-cyanoacetate or acetate via a three-component reaction
Nassiri, Mahmoud
Jalili Milani, Forough
JOURNAL OF CHEMICAL RESEARCH, 2021, 45 (5-6) : 526 - 530

← 1 2 3 4 5 →