FeCl3 catalysed 7-membered ring formation in a single pot: a new route to indole-fused oxepines/azepines and their cytotoxic activity?
Organic & Biomolecular Chemistry Pub Date: 2017-05-04 DOI: 10.1039/C7OB00715A
Abstract
Various oxepine and azepine fused N-heterocyclic derivatives were synthesized using a new and one-pot reaction of 2,3-dichloro quinoxaline/pyrazine with 2-(1H-indol-2-yl)phenol/aniline in the presence of 25 mol% FeCl3. The reaction proceeded via C–C bond followed by C–X (X = O or N) bond formation to construct the central 7-membered ring, affording the desired products in good yields. The structure assignment was confirmed by the single crystal X-ray analysis of a synthesized oxepine fused N-heterocycle derivative. Most of the synthesized compounds were found to be promising when tested for their anti-proliferative properties against cervical and breast cancer cell lines.
Recommended Literature
- [1] Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings Analyst, 1996,121, 785-788 10.1039/AN9962100785
- [2] Evidence for the intrinsic nature of band-gap states electrochemically observed on atomically flat TiO2(110) surfaces? Shintaro Takata,Yoshihiro MiuraPhys. Chem. Chem. Phys., 2014,16, 24784-24789 10.1039/C4CP03280B
- [3] Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications? Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping XieNanoscale Adv., 2020,2, 3921-3932 10.1039/D0NA00381F
- [4] Essential effect of the electrolyte on the mechanical and chemical degradation of LiNi0.8Co0.15Al0.05O2 cathodes upon long-term cycling?? Xiaoming Liu,Zachary D. Hood,Wangda Li,Donovan N. Leonard,Arumugam Manthiram,Miaofang ChiJ. Mater. Chem. A, 2021,9, 2111-2119 10.1039/D0TA07814J
- [5] Distinct impact of glycation towards the aggregation and toxicity of murine and human amyloid-β? Eunju Nam,Jiyeon Han,Sunhee Choi,Mi Hee LimChem. Commun., 2021,57, 7637-7640 10.1039/D1CC02695J
- [6] Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer? Domenico Lombardo,Gianmarco Munaò,Pietro Calandra,Luigi Pasqua,Maria Teresa CaccamoPhys. Chem. Chem. Phys., 2019,21, 11983-11991 10.1039/C9CP02195G
- [7] Excited state dynamics of symmetric and asymmetric Cr3(dpa)4Cl2 measured using femtosecond transient absorption spectroscopy? Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia ChenPhys. Chem. Chem. Phys., 2017,19, 25471-25477 10.1039/C7CP03968A
- [8] Estimation of activation energy for electroporation and pore growth rate in liquid crystalline and gel phases of lipid bilayers using molecular dynamics simulations? Amit Kumar Majhi,Subbarao Kanchi,V. Venkataraman,K. G. Ayappa,Prabal K. MaitiSoft Matter, 2015,11, 8632-8640 10.1039/C5SM02029H
- [9] Excimer formation effects and trap-assisted charge recombination loss channels in organic solar cells of perylene diimide dimer acceptors? Min Kim,Jae-Joon Lee,Tengling Ye,Panagiotis E. Keivanidis,Kilwon ChoJ. Mater. Chem. C, 2020,8, 1686-1696 10.1039/C9TC04955J
- [10] Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements Analyst, 1991,116, 1125-1130 10.1039/AN9911601125
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)