Lewis acid promoted construction of chromen-4-one and isoflavone scaffolds via regio- and chemoselective domino Friedel–Crafts acylation/Allan–Robinson reaction??
Organic & Biomolecular Chemistry Pub Date: 2014-09-16 DOI: 10.1039/C4OB01743A
Abstract
A facile and efficient synthesis of chromen-4-one and isoflavone frameworks is achieved by the domino C-acylation/O-acylation/aldolization sequence. This operationally simple one-pot elegant strategy provides structurally unique chromen-4-ones and isoflavones directly from phenols via concomitant formation of multiple C–C and C–O bonds in a single operation. The outcomes of the buttressing effect, substituent dependence, and catalyst and solvent specificity during the course of the Friedel–Crafts acylation reactions are demonstrated and supported by fitting experiments.
Recommended Literature
- [1] 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
- [2] Estimates of hydride ion stability in condensed systems: energy of formation and solvation in aqueous and polar-organic solvents Craig A. Kelly,David R. RosseinskyPhys. Chem. Chem. Phys., 2001,3, 2086-2090 10.1039/B010092G
- [3] Excitation energies from ground-state density-functionals by means of generator coordinates A. B. F. da Silva,K. CapellePhys. Chem. Chem. Phys., 2009,11, 4564-4569 10.1039/B902529D
- [4] 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
- [5] Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells? Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re AlsbergJ. Mater. Chem. A, 2015,3, 9851-9860 10.1039/C5TA00625B
- [6] Enantio- & chemo-selective preparation of enantiomerically enriched aliphatic nitro alcohols using Candida parapsilosis ATCC 7330 Sowmyalakshmi VenkataramanRSC Adv., 2015,5, 73807-73813 10.1039/C5RA13593A
- [7] 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
- [8] 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
- [9] EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis? Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” KimLab Chip, 2009,9, 1732-1739 10.1039/B821508A
- [10] Enabling stable MnO2 matrix for aqueous zinc-ion battery cathodes? Yiding Jiao,Liqun Kang,Jasper Berry-Gair,Kit McColl,Jianwei Li,Haobo Dong,Hao Jiang,Ryan Wang,Furio Corà,Dan J. L. Brett,Ivan P. ParkinJ. Mater. Chem. A, 2020,8, 22075-22082 10.1039/D0TA08638J
Journal Name：Organic & Biomolecular Chemistry
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)