Tandem Strecker/C(sp3)–H amination reactions for the construction of cyanide-functionalized imidazo[1,5-a]pyridines with NH4SCN as a cyanating agent?
Organic Chemistry Frontiers Pub Date: 2021-09-21 DOI: 10.1039/D1QO01060C
Abstract
An I2O5 promoted tandem Strecker/C(sp3)–H amination reaction of pyridine-2-carboxaldehydes, benzylamines and NH4SCN has been reported. This multicomponent reaction that allows the single-step construction of biologically important cyano-functionalized imidazo[1,5-a]pyridines with molecular diversity was realized for the first time. Moreover, the use of safe and easy-to-handle NH4SCN as a surrogate cyanating agent makes this protocol appealing for potential applications.
![Graphical abstract: Tandem Strecker/C(sp3)–H amination reactions for the construction of cyanide-functionalized imidazo[1,5-a]pyridines with NH4SCN as a cyanating agent](http://scimg.chem960.com/usr/1/D1QO01060C.jpg)
Recommended Literature
- [1] Emerging investigator series: heterogeneous reactions of sulfur dioxide on mineral dust nanoparticles: from single component to mixed components? Tao Wang,Yangyang Liu,Yue Deng,Hongbo Fu,Jianmin ChenEnviron. Sci.: Nano, 2018,5, 1821-1833 10.1039/C8EN00376A
- [2] Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond? Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin LiuChem. Commun., 2018,54, 10092-10095 10.1039/C8CC05410J
- [3] Evolution in surface coverage of CH3NH3PbI3?XClXvia heat assisted solvent vapour treatment and their effects on photovoltaic performance of devices Dhirendra K. Chaudhary,Pramendra Kumar,Lokendra KumarRSC Adv., 2016,6, 94731-94738 10.1039/C6RA18729C
- [4] 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
- [5] Evolution and characterization of a benzylguanine-binding RNA aptamer? J. Xu,T. J. Carrocci,A. A. HoskinsChem. Commun., 2016,52, 549-552 10.1039/C5CC07605F
- [6] Fate of Sb(v) and Sb(iii) species along a gradient of pH and oxygen concentration in the Carnoulès mine waters (Southern France) Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique DesoeuvreEnviron. Sci.: Processes Impacts, 2013,15, 1536-1544 10.1039/C3EM00215B
- [7] Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)? Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. LlewellynChem. Commun., 2007, 3291-3293 10.1039/B703468G
- [8] Examination of deposit in commercial diluted phosphoric acid Analyst, 1880,5, 146-147 10.1039/AN8800500146
- [9] Estimating and correcting interference fringes in infrared spectra in infrared hyperspectral imaging Ghazal Azarfar,Ebrahim Aboualizadeh,Nicholas M. Walter,Simona Ratti,Camilla Olivieri,Alessandra Norici,Michael Nasse,Achim Kohler,Mario GiordanoAnalyst, 2018,143, 4674-4683 10.1039/C8AN00093J
- [10] Evolutionary approaches in protein engineering towards biomaterial construction Brindha J.,Balamurali M. M.,Kaushik ChandaRSC Adv., 2019,9, 34720-34734 10.1039/C9RA06807D
Journal Name：Organic Chemistry Frontiers
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)