Highly regioselective and diastereoselective synthesis of novel pyrazinoindolones via a base-mediated Ugi-N-alkylation sequence?
RSC Advances Pub Date: 2023-06-06 DOI: 10.1039/D3RA02065G
Abstract
An efficient base-mediated/metal-free approach has been developed for the synthesis of 1-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indole-3-carboxamide derivatives via intramolecular indole N–H alkylation of novel bis-amide Ugi-adducts. In this protocol the Ugi reaction of (E)-cinnamaldehyde derivatives, 2-chloroaniline, indole-2-carboxylic acid and different isocyanides was designed for the preparation of bis-amides. The main highlight of this study is the practical and highly regioselective preparation of new polycyclic functionalized pyrazino derivatives. This system is facilitated by Na2CO3 mediation in DMSO and 100 °C conditions.
Recommended Literature
- [1] An aptasensor for detection of potassium ions based on RecJf exonuclease mediated signal amplification Bidou Wang,Xifeng ChenAnalyst, 2014,139, 5695-5699 10.1039/C4AN01350F
- [2] Aggregation, pretransitional behavior, and optical properties in the isotropic phase of lyotropic chromonic liquid crystals studied in high magnetic fields Tanya Ostapenko,Peter J. Collings,Samuel N. Sprunt,J. T. GleesonSoft Matter, 2013,9, 9487-9498 10.1039/C3SM51819A
- [3] An approach to biodegradable star polymeric architectures using disulfide coupling? Jingquan Liu,Huiyun Liu,Zhongfan Jia,Volga Bulmus,Thomas P. DavisChem. Commun., 2008, 6582-6584 10.1039/B817037A
- [4] 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
- [5] An integrated microfluidic 3D tumor system for parallel and high-throughput chemotherapy evaluation? Dan Liu,Rui Hu,Zhongchao Huang,Meilin Sun,Kai HanAnalyst, 2020,145, 6447-6455 10.1039/D0AN01229G
- [6] 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
- [7] An integrated chip for immunofluorescence and its application to analyze lysosomal storage disorders Jie Shen,Ying Zhou,Tu Lu,Junya Peng,Zhixiang Lin,Yuhong Pang,Li YuLab Chip, 2012,12, 317-324 10.1039/C1LC20845D
- [8] An alkynylboronatecycloaddition strategy to functionalised benzyne derivatives? James D. Kirkham,Patrick M. Delaney,George J. Ellames,Eleanor C. Row,Joseph P. A. HarrityChem. Commun., 2010,46, 5154-5156 10.1039/C0CC01345E
- [9] An artificial CO-releasing metalloprotein built by histidine-selective metallation? Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?oChem. Commun., 2015,51, 3993-3996 10.1039/C4CC10204E
- [10] An Aptamer Bio-barCode (ABC) assay using SPR, RNase H, and probes with RNA and gold-nanorods for anti-cancer drug screening Chengbin Yang,Hing Lun Tsang,Pui Man Lau,Ken-Tye Yong,Ho Pui Ho,Siu Kai KongAnalyst, 2017,142, 3579-3587 10.1039/C7AN01026E
Journal Name：RSC Advances
research_products
-
CAS no.: 89640-58-4
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.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)