Synthesis of imidazoles via cascade reaction of nitroallylic acetates with amidines and studies on their trypanocidal activity

被引：0

作者：

Kumar, Tarun ^{[1
]}

Verma, Deepti ^{[1
]}

Menna-Barreto, Rubem F. S. ^{[2
]}

Valenca, Wagner O. ^{[3
]}

da Silva Junior, Eufranio N. ^{[3
]}

Namboothiri, Irishi N. N. ^{[1
]}

机构：

[1] Indian Inst Technol, Bombay 400076, Maharashtra, India

[2] Fiocruz MS, Inst Oswaldo Cruz, BR-21045900 Rio De Janeiro, RJ, Brazil

[3] Univ Fed Minas Gerais, Dept Chem, Inst Exact Sci, BR-31270901 Belo Horizonte, MG, Brazil

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2015年 / 13卷 / 07期

关键词：

MORITA-BAYLIS-HILLMAN; MAP KINASE INHIBITORS; ONE-POT SYNTHESIS; HETEROCYCLIC-DERIVATIVES; REGIOSELECTIVE SYNTHESIS; CYCLOADDITION; NITROALKENES; COMPLEXES; TANDEM; IMIDAZOPYRIDINES;

D O I：

10.1039/c4ob02561j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot, two step synthesis of highly substituted imidazoles has been carried out in good to excellent yields for the first time via a cascade intermolecular aza-S(N)2'-intramolecular aza-Michael addition involving a variety of Morita-Baylis-Hillman acetates of nitroalkenes and amidines in the presence of DABCO at room temperature. The synthetic and biological utility of the products has been demonstrated. In particular, some of the imidazoles exhibited potent activity against T. cruzi, the etiological agent of Chagas disease.

引用

页码：1996 / 2000

页数：5

共 50 条

[21] Synthesis of indolequinones via a Sonogashira coupling/cyclization cascade reaction
Yamashita, Mitsuaki
Ueda, Kazunori
Sakaguchi, Koichi
Iida, Akira
TETRAHEDRON LETTERS, 2011, 52 (36) : 4665 - 4670
[22] A Formal Synthesis of Ezetimibe via Cycloaddition/Rearrangement Cascade Reaction
Michalak, Michal
Stodulski, Maciej
Stecko, Sebastian
Mames, Adam
Panfil, Irma
Soluch, Magdalena
Furman, Bartlomiej
Chmielewski, Marek
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (16): : 6931 - 6936
[23] Regioselective Synthesis of Highly Substituted Imidazoles via the Sequential Reaction of Allenyl Sulfonamides and Amines
Yu, Lian
Deng, Yuan
Cao, Jian
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (09): : 4729 - 4735
[24] Synthesis of trisubstituted imidazoles via a convergent reaction network from methyl ketones and benzoins
Xue, Wei-Jian
Li, Hong-Zheng
Gao, Fang-Fang
Wu, Anxin
TETRAHEDRON, 2014, 70 (02) : 239 - 244
[25] Studies on synthesis of multiaryl-substituted imidazoles and reversal activity on the multidrug resistance
Ruan, JW
Fu, LW
Huang, ZS
Chen, LM
Ma, L
Gu, LQ
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2004, 25 (05): : 870 - 873
[26] Asymmetric synthesis of pyrano[2,3-c]pyrazoles via a cascade reaction between Morita-Baylis-Hillman acetates of nitroalkenes and pyrazolones
Xie, Jin
Sha, Feng
Wu, Xin-Yan
TETRAHEDRON, 2016, 72 (27-28) : 4047 - 4054
[27] Gallic Acid Alkyl Esters: Trypanocidal and Leishmanicidal Activity, and Target Identification via Modeling Studies
Steverding, Dietmar
do Nascimento, Lazaro Gomes
Perez-Castillo, Yunierkis
de Sousa, Damiao Pergentino
MOLECULES, 2022, 27 (18):
[28] Palladium-Catalyzed Reaction of MBH Acetates and Terminal Alkynes: Cascade Synthesis of Phenanthridine and 6-Arylethynylphenanthridine
Gupta, Tanu
Singh, Jay Bahadur
Singh, Rashmi
Singh, Radhey M.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (31) : 4284 - 4295
[29] A Facile FeCl3/I2-Catalyzed Aerobic Oxidative Coupling Reaction: Synthesis of Tetrasubstituted Imidazoles from Amidines and Chalcones
Zhu, Yuelu
Li, Cheng
Zhang, Jidong
She, Mengyao
Sun, Wei
Wan, Kerou
Wang, Yaqi
Yin, Bin
Liu, Ping
Li, Jianli
ORGANIC LETTERS, 2015, 17 (15) : 3872 - 3875
[30] Synthesis of New Dehydrodieugenol Derivatives via Olefin Cross Metathesis and In Vitro Evaluation of Their Trypanocidal Activity
Galhardo, Thalita S.
Ueno, Anderson K.
Carvalho, Wagner A.
Costa-Silva, Thais A.
Goncalves, Marina M.
Abiuzi, Mariana B.
Tempone, Andre G.
Lago, Joao Henrique G.
Mandelli, Dalmo
Fischmeister, Cedric
Bruneau, Christian
CATALYSTS, 2023, 13 (07)

← 1 2 3 4 5 →