I2-Mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides: selective synthesis of iodine-functionalized and non-iodine-functionalized fused imidazoles?
Organic Chemistry Frontiers Pub Date: 2022-01-25 DOI: 10.1039/D1QO01940F
Abstract
An I2-mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides has been demonstrated. This strategy involves C![[triple bond, length as m-dash]](https://www.rsc.org/images/entities/char_e002.gif)
N bond cleavage of isocyanides and can selectively synthesize iodine-functionalized and non-iodine-functionalized fused imidazoles. Scale-up experiments and arylation, alkynylation, alkenylation and selenization of iodine-functionalized products demonstrated the potential applications of this reaction.
![Graphical abstract: I2-Mediated [3 + 2] annulation of methyl-azaarenes with alkyl 2-isocyanoacetates or amino acid ester hydrochlorides: selective synthesis of iodine-functionalized and non-iodine-functionalized fused imidazoles](http://scimg.chem960.com/usr/1/D1QO01940F.jpg)
Recommended Literature
- [1] Emergence of microfluidic wearable technologies Joo Chuan Yeo,KenryLab Chip, 2016,16, 4082-4090 10.1039/C6LC00926C
- [2] Establishing the accuracy of position-specific carbon isotope analysis of propane by GC-pyrolysis-GC-IRMS ChangjieLiu,PengLiu,XiaofengWang,XiaoqiangLi,JuskeHorita 10.1002/rcm.9494
- [3] Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage? M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. KaskelJ. Mater. Chem. A, 2015,3, 17983-17990 10.1039/C5TA03730A
- [4] Ester-mediated peptide formation promoted by deep eutectic solvents: a facile pathway to proto-peptides? Chen-Yu Chien,Sheng-Sheng YuChem. Commun., 2020,56, 11949-11952 10.1039/D0CC03319G
- [5] Excellent kinetics of single-phase Gd-doped ceria fuel electrodes in solid oxide cells? Andreas Nenning,Manuel Holzmann,Jürgen Fleig,Alexander K. OpitzMater. Adv., 2021,2, 5422-5431 10.1039/D1MA00202C
- [6] Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering? Jing Yu,Yu-Qi Lyu,Jiapeng Liu,Mohammed B. Effat,Junxiong WuJ. Mater. Chem. A, 2019,7, 17995-18002 10.1039/C9TA03784E
- [7] Excimer–monomer switch: a reaction-based approach for selective detection of fluoride? Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi CaoAnalyst, 2014,139, 3588-3592 10.1039/C4AN00522H
- [8] 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
- [9] Fatty acid eutectic mixtures and derivatives from non-edible animal fat as phase change materials? Pau Gallart-Sirvent,Marc Martín,Gemma Villorbina,Mercè Balcells,Aran Solé,Luisa F. Cabeza,Ramon Canela-GarayoaRSC Adv., 2017,7, 24133-24139 10.1039/C7RA03845C
- [10] Dissolution of cork biopolymers in biocompatible ionic liquids Helga Garcia,Rui Ferreira,Marija Petkovic,Jamie L. Ferguson,Maria C. Leit?o,H. Q. Nimal Gunaratne,Luís Paulo N. RebeloGreen Chem., 2010,12, 367-369 10.1039/B922553F
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)