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
收藏
页数：16
相关论文
共 50 条
  • [31] 2-[2-(1H-indol-3-yl)ethyliminiomethyl]-4-nitrophenolate
    Ali, Hapipah M.
    Mustafa, M. I. Mohamed
    Rizal, M. Razali
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O913 - U2590
  • [32] The effect of hydrogen bonding on the conformations of 2-(1H-indol-3-yl)-2-oxoacetamide and 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide
    Sonar, Vijayakumar N.
    Parkin, Sean
    Crooks, Peter A.
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2012, 68 : O405 - U226
  • [33] Synthesis and in-vitro antimicrobial screening of 3-cinnamoyl coumarin and 3-[3-(1H-indol-2-yl)-3-aryl-propanoyl]-2H-chromen-2-ones
    Gholap, Somnath S.
    Deshmukh, Umesh P.
    Tambe, Macchindra S.
    IRANIAN JOURNAL OF CATALYSIS, 2013, 3 (03): : 171 - 176
  • [34] 2-(6-Chloro-1H-indol-3-yl)acetonitrile
    Li, Jin-Feng
    Luo, Yang-Hui
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68
  • [35] 2-(7-Methyl-1H-indol-3-yl)acetonitrile
    Ge, Yu-Hua
    Pan, Mei-Ling
    Xu, Jian
    Luo, Yang-Hui
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68
  • [36] 2-(4-Bromo-1H-indol-3-yl)acetonitrile
    Mao, Qiu-Xia
    Zhang, Chen-Guang
    Li, Jin-Feng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68 : O451 - U1075
  • [37] 2-(4-Chloro-1H-indol-3-yl)acetonitrile
    Pan, Mei-Ling
    Li, Xiang
    Luo, Yang-Hui
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68
  • [38] 2-(4-Methoxy-1H-indol-3-yl)acetonitrile
    Lu, Yong-Hong
    Pan, Mei-Ling
    Luo, Yang-Hui
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2012, 68
  • [39] Calorimetric and computational study of (1H-Indol-n-yl)methanol and 2-(1H-Indol-n-yl)ethanol (n=2, 3)
    Carvalho, Tania M. T.
    Amaral, Luisa M. P. F.
    Morais, Victor M. F.
    Ribeiro da Silva, Maria D. M. C.
    THERMOCHIMICA ACTA, 2019, 673 : 169 - 176
  • [40] 3-(1H-indol-3-yl)-2-[3-(4-methoxybenzoyl)-thioureido]propionic acid
    Ngah, N
    Dariman, N
    Yamin, BM
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O1025 - O1027
12345