An eco-friendly approach for the synthesis of 1,2,5-trisubstituted and 4-amino-1,2,5-tetrasubstituted imidazoles via a multi-component condensation

被引：6

作者：

Mehrabi, Hossein ^{[1
]}

Alizadeh-Bami, Farzaneh ^{[1
]}

Meydani, Azam ^{[1
]}

Besharat, Soheila ^{[1
]}

机构：

[1] Vali E Asr Univ Rafsanjan, Dept Chem, Rafsanjan 77176, Iran

来源：

ARKIVOC | 2021年

关键词：

Multi-component condensation; 1,2,5-trisubstituted imidazole; 4-amino-1,2,5-tetrasubstituted imidazole; arylglyoxal; ethyl bromopyruvate; ONE-POT SYNTHESIS; POLYSUBSTITUTED IMIDAZOLES; CATALYST; AMINOIMIDAZOLE; DERIVATIVES; EFFICIENT; AGENTS; DRUG;

D O I：

10.24820/ark.5550190.p011.442

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 1,2,5-trisubstituted and 4-amino-1,2,5-tetrasubstituted imidazoles was demonstrated via a two-step cyclo-condensation reaction of aryl amines, carbonitriles, and ethyl bromopyruvate or aryl amines and arylglyoxals in ethanol heated under reflux in the presence of iron (III) chloride (FeCl3), and disodium phosphate (Na2HPO4) as catalysts, respectively. All the products were obtained in good to excellent yields and their structures were established from their spectroscopic data. [GRAPHICS] .

引用

页码：86 / 95

页数：10

共 50 条

[41] Copper-catalyzed aerobic benzylic sp3 C-H oxidation mediated synthesis of 2,4,5-trisubstituted imidazoles via a domino multi-component reaction
Jayram, Janeeka
Jeena, Vineet
GREEN CHEMISTRY, 2017, 19 (24) : 5841 - 5845
[42] One-Pot Coupling-Cyclization-Alkylation Synthesis of 1,2,5-Trisubstituted 7-Azaindoles in a Consecutive Three-component Fashion
Lessing, Timo
Mueller, Thomas J. J.
SYNLETT, 2017, 28 (14) : 1743 - 1747
[43] Design of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as a dual-catalyst for the one-pot multi-component synthesis of 1,2,4,5-tetrasubstituted imidazoles
Zolfigol, Mohammad Ali
Khazaei, Ardeshir
Moosavi-Zare, Ahmad Reza
Zare, Abdolkarim
Asgari, Zhila
Khakyzadeh, Vahid
Hasaninejad, Alireza
JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY, 2013, 19 (03) : 721 - 726
[44] One-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles by a tandem three-component reaction of hydroxylamines, aldehydes and 2-azido acrylates
Hu, Bao
Ai, Ning
Wang, Zhao
Xu, Xiaoliang
Li, Xiaonian
ARKIVOC, 2012, : 222 - 228
[45] Facile One Pot Multi-Component Solvent-Free Synthesis of 2,4,5-Trisubstituted Imidazoles Using “Green” and Expeditious Ionic Liquid Catalyst under Microwave Irradiation
B. Sonyanaik
K. Ashok
S. Rambabu
D. Ravi
A. Kurumanna
P. Madhu
B. Sakram
Russian Journal of General Chemistry, 2018, 88 : 537 - 540
[46] Facile One Pot Multi-Component Solvent-Free Synthesis of 2,4,5-Trisubstituted Imidazoles Using "Green" and Expeditious Ionic Liquid Catalyst under Microwave Irradiation
Sonyanaik, B.
Ashok, K.
Rambabu, S.
Ravi, D.
Kurumanna, A.
Madhu, P.
Sakram, B.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2018, 88 (03) : 537 - 540
[47] Synthesis of 1,2,4,5-tetrasubstituted imidazoles and 2,4,5,6-tetrasubstituted pyrimidines: three-component, the one-pot reaction of arylamidines, malononitrile, and arylglyoxals or aryl aldehydes
Mehrabi, Hossein
Hajipour, Mina
Rezazadeh-Jabalbarezi, Fatemeh
Alizadeh-Bami, Farzaneh
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (09) : 3361 - 3368
[48] Ag–TiO2 nanocomposite-catalyzed one-pot synthesis of 1,2,4,5-tetrasubstituted imidazoles: a green and benign approach
Soghra Alipour
Seyed Mohammad Vahdat
Fereshteh Chekin
Journal of the Iranian Chemical Society, 2021, 18 : 2315 - 2321
[49] Synthesis and reactivity of azidoximes: III. 1-azido(4-amino-1,2,5-oxadiazol-3-yl)aldoxime in the cycloaddition reaction
Romanova, TV
Mel'nikova, SF
Tselinskii, IV
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 39 (04) : 574 - 578
[50] A CONVENIENT SYNTHESIS OF 1,2,5-TRISUBSTITUTED 4,5-DIHYDROIMIDAZOLES AND 1,3-DIAZASPIRO[4.4(5)]ALK-2-ENES FROM N-ALKYLIDENEANILINES
SHAWKAT, S
SHARMA, S
SYNTHESIS-STUTTGART, 1992, (07): : 664 - 666

← 1 2 3 4 5 →