Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines?
Organic & Biomolecular Chemistry Pub Date: 2018-05-22 DOI: 10.1039/C8OB00588E
Abstract
The polyphosphoric acid-mediated reaction of 2-(2-aminophenyl)indenes with nitroalkenes was tested in the frame of synthetic studies towards CDK inhibitors with the paullone core. Unexpectedly, this reaction proceeded via a different mechanistic pathway affording derivatives of the natural alkaloid isocryptolepine. The scope of this unusual transformation was investigated and a mechanistic rationale explaining this outcome is offered.
![Graphical abstract: Unexpected cyclization of 2-(2-aminophenyl)indoles with nitroalkenes to furnish indolo[3,2-c]quinolines](http://scimg.chem960.com/usr/1/C8OB00588E.jpg)
Recommended Literature
- [1] An approach to 7-aza-1-phosphanorbornane complexes: strain promoted rearrangement of 1-iminylphosphirane complexes and cycloaddition with olefins? Yang Xu,Min Wang,Donghui Wei,Rongqiang Tian,Zheng Duan,Fran?ois MatheyDalton Trans., 2019,48, 5523-5526 10.1039/C9DT00838A
- [2] An analyte-triggered artificial peroxidase system based on dimanganese complex for a versatile enzyme assay? Suji Lee,Min Su HanChem. Commun., 2021,57, 9450-9453 10.1039/D1CC03638F
- [3] An apparatus for determining small amounts of alchohol in sour milk and urine Analyst, 1964,89, 272-275 10.1039/AN9648900272
- [4] An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis? Supaporn Sawadjoon,Joseph S. M. SamecOrg. Biomol. Chem., 2011,9, 2548-2554 10.1039/C0OB00383B
- [5] An astrophysically-relevant mechanism for amino acid enantiomer enrichment Stephen P. Fletcher,Richard B. C. Jagt,Ben L. FeringaChem. Commun., 2007, 2578-2580 10.1039/B702882B
- [6] An all-solid-state imprinted polymer-based potentiometric sensor for determination of bisphenol S? Rongning Liang,Tanji Yin,Ruiqing Yao,Wei QinRSC Adv., 2016,6, 73308-73312 10.1039/C6RA14461F
- [7] Aluminium alkyl and aryloxide complexes of pyrazine and bipyridines: synthesis and structure? Doug Ogrin,Laura H. van Poppel,Simon G. Bott,Andrew R. BarronDalton Trans., 2004, 3689-3694 10.1039/B410662H
- [8] An investigation of the electrochemical delithiation process of carbon coated α-Fe2O3nanoparticles Adrian Brandt,Florian Winter,Sebastian Klamor,Frank Berkemeier,Jatinkumar Rana,Rainer P?ttgen,Andrea BalducciJ. Mater. Chem. A, 2013,1, 11229-11236 10.1039/C3TA11821E
- [9] An atlas of endohedral Sc2S cluster fullerenes? Li-Hua Gan,Rui Wu,Jian-Lei Tian,Patrick W. FowlerPhys. Chem. Chem. Phys., 2017,19, 419-425 10.1039/C6CP07370K
- [10] An apparatus for testing water by measurement of its electrical conductivity Analyst, 1912,37, 538-543 10.1039/AN9123700538
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)