Synthesis of 2-(1H-Indol-2-yl)acetamides via Bronsted Acid-Assisted Cyclization Cascade

被引：15

作者：

Aksenov, Nicolai A. ^{[1
]}

Aksenov, Dmitrii A. ^{[1
]}

Skomorokhov, Anton A. ^{[1
]}

Prityko, Lidiya A. ^{[1
]}

Aksenov, Alexander V. ^{[1
]}

Griaznov, Georgii D. ^{[2
]}

Rubin, Michael ^{[1
,2
]}

机构：

[1] North Caucasus Fed Univ, Dept Chem, Stavropol 355009, Russia

[2] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 19期

基金：

俄罗斯科学基金会;

关键词：

INHIBITORY-ACTIVITY; MICHAEL ADDITION; HISTONE; 2'-AMINOCHALCONES; NITROSTYRENES; REDUCTION; DISCOVERY; EFFICIENT; INDOLES; ROUTE;

D O I：

10.1021/acs.joc.0c01344

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and straightforward Bronsted-acid mediated cascade process was developed, involving cyclization of readily available beta-ketonitriles into 2-aminofurans, and their subsequent recyclization into 2-(1H-indol-2-yl)acetamides is developed. This synthetic route opens a new avenue for an expeditious assembly of

引用

页码：12128 / 12146

页数：19

共 50 条

[31] Synthesis of 2-{2-[(α/β-naphthalen-1-ylsulfonyl)amino]-1,3-thiazol-4-yl} acetamides with 11β-hydroxysteroid dehydrogenase inhibition and in combo antidiabetic activities
Navarrete-Vazquez, Gabriel
Guadalupe Morales-Vilchis, Maria
Estrada-Soto, Samuel
Jose Ramirez-Espinosa, Juan
Hidalgo-Figueroa, Sergio
Nava-Zuazo, Carlos
Tlahuext, Hugo
Leon-Rivera, Ismael
Medina-Franco, Jose L.
Lopez-Vallejo, Fabian
Webster, Scott P.
Binnie, Margaret
Ortiz-Andrade, Rolffy
Moreno-Diaz, Hermenegilda
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 74 : 179 - 186
[32] A Facile One-Pot Four-Component Green Synthesis of 4-(1H-Indol-2-yl)-4H-chromenes Conjugated with Phthalazine-1,4-diones
Dhavaria, S.
Dhiman, M.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (04) : 726 - 732
[33] Facile synthesis of 9H-pyrrolo[1,2-a]indoles via Bronsted acid catalyzed cascade reactions
Xu, Kunhua
Chen, Wenming
Lin, Jin
Chen, Guifang
Wang, Biao
Tian, Xu
CHEMICAL COMMUNICATIONS, 2019, 55 (97) : 14613 - 14616
[34] Synthesis of indole-2-carbohydrazides and 2-(indol-2-yl)-1,3,4-oxadiazoles as antioxidants and their acetylcholinesterase inhibition properties
Murat Bingul
Mehmet F. Saglam
Hakan Kandemir
Mehmet Boga
Ibrahim F. Sengul
Monatshefte für Chemie - Chemical Monthly, 2019, 150 : 1553 - 1560
[35] Cascade Oxidative Trifluoromethylthiolation and Cyclization of 3-Alkyl-1-(2-(alkynyl)phenyl)indoles
Uppalabat, Thikhamporn
Hassa, Nattawoot
Sawektreeratana, Natthapat
Leowanawat, Pawaret
Janthakit, Pattarapapa
Nalaoh, Phattananawee
Promarak, Vinich
Soorukram, Darunee
Reutrakul, Vichai
Kuhakarn, Chutima
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (09) : 5403 - 5419
[36] An Efficient and Rapid Microwave-Assisted Synthesis of 1-acetyl-1H-indol-3-yl Acetates
Parshotam, Jay P.
Brazier, John A.
Bovill, Richard
Osborn, Helen M. I.
CURRENT MICROWAVE CHEMISTRY, 2016, 3 (03) : 247 - 257
[37] Copper-catalyzed intramolecular redox reaction: Asymmetric synthesis of chiral 2-(1H-pyrrol-1-yl)-mandelic acid esters
Du, Hong-Jin
Lin, Chao
Wen, Xiaoan
Xu, Qing-Long
TETRAHEDRON, 2018, 74 (52) : 7480 - 7484
[38] Synthesis, Structure and Biological Activity of 2-[2-(4-Fluorobenzylidene)hydrazinyl]-4-(1-methyl-1H-indol-3-yl)thieno[3,2-d]pyrimidine
Shi Jian-Tao
Gong Yi-Lin
Li Jun
Wang Yang
Chen Ye
Ding Shi
Liu Ju
CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2019, 38 (09) : 1530 - 1536
[39] Facile synthesis of 11-aryl-6H-isoindolo[2,1-a]-indol-6-ones via hypervalent iodine(III)-promoted cascade cyclization
Dev, Kapil
Maurya, Rakesh
RSC ADVANCES, 2015, 5 (17) : 13102 - 13106
[40] Cascade and multicomponent synthesis of structurally diverse 2-(pyrazol-3-yl)pyridines and polysubstituted pyrazoles
Barroso, Raquel
Cabal, Maria-Paz
Jimenez, Azucena
Valdes, Carlos
ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (08) : 1629 - 1636

← 1 2 3 4 5 →