Facile, one-pot, four-component synthesis of a new series of imidazo[1,2-a]pyridines in presence of TPAB in EtOH under reflux conditions

被引：10

作者：

Etivand, Nasser ^{[1
]}

Khalafy, Jabbar ^{[1
]}

Marjani, Ahmad Poursattar ^{[1
]}

机构：

[1] Urmia Univ, Dept Organ Chem, Fac Chem, Orumiyeh 5756151818, Iran

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2019年 / 45卷 / 06期

关键词：

Imidazo[1; 2-a]pyridines; 2-Aminopyridine; Aryl glyoxal monohydrates; Ethyl acetoacetate; Hydrazine hydrate; One-pot four-component reaction; TPAB; MICROWAVE-ASSISTED SYNTHESIS; CATALYZED SYNTHESIS; DERIVATIVES; RECEPTOR; CONVENIENT; DISCOVERY; PYRIDINES; BINDING;

D O I：

10.1007/s11164-019-03797-1

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A convenient, regioselective, novel, and elegant one-pot, four-component reaction was designed for synthesis of a series of new of imidazo[1,2-a]pyridines using aryl glyoxal monohydrates, ethyl acetoacetate, hydrazine hydrate, and 2-aminopyridine in presence of tetrapropylammonium bromide under reflux in EtOH as solvent. The main advantages of this protocol include the availability and low cost of the starting materials, short reaction time, convenient operation, easy workup process, highly facile operation, nonhazardous byproducts, and high yield (82-94%). [GRAPHICS] .

引用

页码：3379 / 3394

页数：16

共 50 条

[31] A facile one-pot, four-component synthesis of (Z)-isomer of rhodanine-oxindole derivatives under environmentally benevolent conditions
Moghaddam, F. Matloubi
Aghamiri, Bagher
Jalalinik, Mahbod
SYNTHETIC COMMUNICATIONS, 2022, 52 (02) : 175 - 184
[32] New simple and one-pot synthetic routes to polyfunctionally substituted imidazo-[1,2-a]pyridines, pyrido[1,2-a]pyrimidines, pyrido[1,2-a]-1,3- diazepines, and imidazo[1,2-a]pyrimidines
Hammouda M.
Abou Zeid Z.M.
Metwally M.A.
Chemistry of Heterocyclic Compounds, 2005, 41 (12) : 1525 - 1528
[33] An Unexpected Diastereoselective Synthesis of Novel Substituted Pyridines via One-Pot, Four-Component Reaction
Zangouei, Mahdieh
Esmaeili, Abbas Ali
Mague, Joel T.
SYNLETT, 2016, 27 (11) : 1669 - 1673
[34] One-Pot Three-Component Synthesis of 3-Aminoimidazo[1,2-a]pyridines and -pyrazines in the Presence of Silica Sulfuric Acid
Ahmad Shaabani
Ebrahim Soleimani
Ali Maleki
Monatshefte für Chemie - Chemical Monthly, 2007, 138 : 73 - 76
[35] One-pot three-component synthesis of 3-aminoimidazo[1,2-a]pyridines and -pyrazines in the presence of silica sulfuric acid
Shaabani, Ahmad
Soleimani, Ebrahim
Maleki, Ali
MONATSHEFTE FUR CHEMIE, 2007, 138 (01): : 73 - 76
[36] Microwave-assisted synthesis of novel 2,3-disubstituted imidazo[1,2-a] pyridines via one-pot three component reactions
Karamthulla, Shaik
Khan, Md. Nasim
Choudhury, Lokman H.
RSC ADVANCES, 2015, 5 (25) : 19724 - 19733
[37] Facile Synthesis of Novel Hexahydroimidazo[1,2-a]pyridine Derivatives by One-Pot, Multicomponent Reaction under Ambient Conditions
Tan, Hongbo
Wang, Yinfeng
ACS COMBINATORIAL SCIENCE, 2020, 22 (09) : 468 - 474
[38] Efficient one-pot synthesis of functionalised imidazo[1,2-a]pyridines and unexpected synthesis of novel tetracyclic derivatives by nucleophilic aromatic substitution
Changunda, Charles R. K.
Venkatesh, B. C.
Mokone, William K.
Rousseau, Amanda L.
Brady, Dean
Fernandes, Manuel A.
Bode, Moira L.
RSC ADVANCES, 2020, 10 (14) : 8104 - 8114
[39] Synthesis of Catalyst Using Bio-benign Precursors and Its Application in One-Pot Catalytic Synthesis of Imidazo[1,2-a]pyridines
Mishra, Santosh
Parikh, Anuvasita
Rangan, Krishnan
Sah, Ajay K.
CHEMISTRYSELECT, 2023, 8 (10):
[40] A one-pot, pseudo four-component synthesis of novel benzopyrano[2,3-b]pyridines under solvent-free conditions
Olyaei, Abolfazl
Vaziri, Mohsen
Razeghi, Reza
TETRAHEDRON LETTERS, 2013, 54 (15) : 1963 - 1966

← 1 2 3 4 5 →