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

[1] Imidazoles from nitroallylic acetates and α-bromonitroalkenes with amidines: synthesis and trypanocidal activity studies
Gopi, Elumalai
Kumar, Tarun
Menna-Barreto, Rubem F. S.
Valenca, Wagner O.
da Silva Junior, Eufranio N.
Namboothiri, Irishi N. N.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (38) : 9862 - 9871
[2] Cascade regioselective synthesis of pyrazoles from nitroallylic acetates and N-tosyl hydrazine
Shao, Nana
Chen, Tong
Zhang, Taotao
Zhu, Huajian
Zheng, Qunxiong
Zou, Hongbin
TETRAHEDRON, 2014, 70 (04) : 795 - 799
[3] Synthesis of Functionalized Arenopyrans and Arenylsulfanes via Reaction of Nitroallylic Acetates with Arenols and Arenethiols (vol 41, pg 5735, 2018)
Basu, Pallabita
Sikdar, Robi
Kumar, Tarun
Namboothiri, Irishi N. N.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (33) : 5469 - 5470
[4] Bifunctional Squaramide-Catalyzed Asymmetric Cascade Reaction of Benzothiazoles with 2-Nitroallylic Acetates or Nitroenynes
Song, Xiaoxiao
Qin, Wei
Wang, Xuyang
Luo, Gen
Ni, Qijian
ORGANIC LETTERS, 2023, 25 (51) : 9164 - 9169
[5] Cascade reaction for 3-pyrrolines and pyrroles from nitroallylic acetates and N-mesyl 2-aminoethanones
Chen, Tong
Shao, Nana
Zhu, Huajian
Zhang, Boya
Zou, Hongbin
TETRAHEDRON, 2013, 69 (49) : 10558 - 10564
[6] SYNTHESIS OF IMIDAZOLES BY REACTION OF N-BENZYLATED AMIDINES WITH CARBOXYLIC-ACID DERIVATIVES
LIEBSCHER, J
FEIST, K
JOURNAL FUR PRAKTISCHE CHEMIE, 1988, 330 (02): : 175 - 181
[7] Morita-Baylis-Hillman (MBH) Reaction Derived Nitroallylic Alcohols, Acetates and Amines as Synthons in Organocatalysis and Heterocycle Synthesis
Huang, Wan-Yun
Anwar, Shaik
Chen, Kwunmin
CHEMICAL RECORD, 2017, 17 (03): : 363 - 381
[8] Atropisomerism of α,β-Unsaturated Amidines: Stereoselective Synthesis by Catalytic Cascade Reaction and Optical Resolution
Shindoh, Naoya
Takemoto, Yoshiji
Takasu, Kiyosei
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (29) : 7026 - 7030
[9] THE SYNTHESIS OF IMIDAZOLES VIA THE RADZISZEWSKI REACTION IN AQUEOUS MEDIA
Hernandez Munoz, July A.
dos Santos, Bruno Dias de C. F.
Soares, Renata F.
de Carvalho, Erika M.
Jones Junior, Joel
da Silva, Flavia M.
HETEROCYCLIC LETTERS, 2011, 1 (04): : 365 - 371
[10] Synthesis of Fully Substituted 5-(o-Hydroxybenzoyl)imidazoles via Iodine-Promoted Domino Reaction of Aurones with Amidines
Xu, Hui
Chen, Hong
Hu, Xiao
Xuan, Guang
Li, Pinhua
Zhang, Ze
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (24): : 16204 - 16212

← 1 2 3 4 5 →