Aim of my work is to synthesis of Molecule 2 (Fluoroquinolone) using diphenyl ether as catalyst. Even after several attempts the molecule 2 fails to form due to deactivation of para position by NO2 group in the ring. Few chemistry professors suggested the use of AlCl3 as a catalyst (According to Friedel craft Acylation) . Is it okay to use AlCl3 as catalyst for cyclization reaction. if not please suggest a better catalyst for the case. Herewith i attached image of my reaction scheme.
First convert ester in to corresponding acid chloride and then you use anhydrous aluminum chloride. Or directly you can try with freshly prepared PPA.
Hi Bala, that position is quite deactivated. It's worth a try with AlCl3, but not in catalytic amounts, perhaps try 1.5 - 2 eq. You could also try dissolving your compound in a mixture of TFA/TFAA. I think ultimately you will have to hydrolyse the esters, try the reaction with a better leaving group. You could also try dissolving your compound in a mixture of TFA/TFAA. If all else fails you could try and make the acid chloride (use 1 eq of SOCl2 with the acid). I found this review quite helpful
https://www.beilstein-journals.org/bjoc/articles/6/6
Best of luck
Paddy
You can use AlCl3 for intramulecular cyclization in Friedel-Craft,s acylation reaction and Wagner Meerwein rearrangement involving the formation of Admantane.
Hi Bala, you can try PPA for cyclization which can act both catalyst and solvent.
First convert ester in to corresponding acid chloride and then you use anhydrous aluminum chloride. Or directly you can try with freshly prepared PPA.
Hi Bala, you can use Urea, Thiorea, Semicarbazide , CS2 and Hydrazine for cyclization as well as use ethanol as solvent and sodium hydroxide as catalyst. good luck
yes Bala , and you can use other conditions for cyclization like [ Cu(CH3COO) WITH PYRIDINE ,, OR POCl3 , OTHER conditions from my published chapter ...
The m-F and p-NO2 make the phenyl electron-deficient, thus it is difficult for the Friedel-Craft acylation to take place. It is possible, however, to run the reaction in the absence of solvent by using sodium chloride as an additive at elevated temperatures.
Hi Bala, you can use AlCl3 with POCl3 for cyclization reactions
good luck
You can use AlCl3 a catalyst for cyclization reaction in electrophilic substitution reactions. The reaction must be under anhydrous condition. Solvent used such as nitrobenzene POCl3
- Badges
- Science topic
- Similar topics
- Chemistry
- Organic Chemistry