221665-91-4

Upstream product

• 95060-80-3 1-benzyl-3-hydrazinoisatin 
• 3377-71-7 N-benzylindole 
• 100-39-0 benzyl bromide 
• 91-56-5 indole-2,3-dione 
• 1239497-29-0 N-benzyl-2,2-difluoro-2-iodo-N-phenylacetamide 

Downstream Products

• 197067-27-9 3,3-difluoro-1,3-dihydro-2H-indol-2-one 

Relevant academic research and scientific papers

Solvent Effects: Syntheses of 3,3-Difluorooxindoles and 3-Fluorooxindoles from Hydrazonoindolin-2-one by Selectfluor

Efficient syntheses of 3,3-difluorooxindoles and 3-fluorooxindoles via fluorination of hydrazonoindolin-2-one with Selectfluor are reported. Under different solvent conditions, this method produced 3,3-difluorooxindoles and 3-fluorooxindoles selectively. The broad substrate scope and mild reaction conditions make this transformation a valuable method in drug discovery and development.

Selective fluorination method for isatin hydrazones compounds

The invention discloses a selective fluorination method for an isatin hydrazones compound. The method comprises the steps that one pot reaction is carried out on isatin hydrazone, 1-chloromethyl-4-fluorine-1,4-diazabicyclo [2.2.2] octane bis (tetrafluoroborate) salt and alkali compounds, corresponding 3,3-difluoro indolone and fluorooxindole fluorination products are selectively synthesized; the method fills up technical gaps in the prior art that isatin hydrazones compound is selectively synthesized by using a three-position single fluorination or double fluorination technology starting fromisatin, the operation is simple, the process is short, the product yield is high, and industrial production requirements are met.

Direct conversion of indoles to 3,3-difluoro-2-oxindoles via electrophilic fluorination

3,3-Difluoro-2-oxindoles can be obtained directly from indoles in moderate yields via electrophilic fluorination using N-fluorobenzenesulfonimide as a mild fluorinating reagent. The presence of tert-butyl hydroperoxide during the reaction, together with additional heating after quenching the reaction with triethylamine, is beneficial to the formation of the desired product.

Copper-mediated fluoroalkylation reactions with iododifluoroacetamides: Controlling the selectivity among cross-coupling, intramolecular cyclization, and homocoupling reactions

Cu-mediated fluoroalkylation reactions with iododifluoroacetamides 1 have been systematically investigated. It was found that three types of reactions may coexist in Cu-mediated reactions between iododifluoroacetamides and aryl/alkenyl iodides: cross-coupling, intramolecular cyclization, and homocoupling reactions. The selectivity among these three types of reactions could be controlled by tuning the substituents on the nitrogen atom of iododifluoroacetamides, and/or by removing the cross-coupling reaction partner (aryl/alkenyl halides). The general rule is as follows: (a) in the presence of proper aryl/alkenyl iodides, the cross-coupling products 2 (or 6) are generally formed as the major products; (b) in the absence of aryl/alkenyl iodides, and when R1 = alkyl and R2 = aryl groups, or when R 1 = R2 = aryl groups, the intramolecular cyclization products 3 can be formed predominantly; and (c) in the absence of aryl/alkenyl iodides, and when R1 = R2 = alkyl groups, or when R 1 = H and R2 = alkyl, aryl groups, the homocoupling products 4 can be formed dominantly. Our experimental results also indicate that in many cases when cross-coupling, homocoupling, and intramolecular cyclization reactions coexist in the Cu-mediated reaction system, the reactivity decreases in the following order: cross-coupling > intramolecular cyclization > homocoupling.

Nucleophilic di- and tetrafluorination of dicarbonyl compounds

Reactions of various diketo compounds with Deoxofluor [(CH3OCH2CH2)2NSF3] have been investigated. When reacted with Deoxofluor, α-diketones, R1COCOR2 (R1 = R2/su