3488-44-6

Upstream product

• 115168-89-3 3-(4-fluorophenyl)-3-oxopropanal 
• 186581-53-3 diazomethane 
• 403-43-0 4-fluorobenzoyl chloride 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 1493-51-2 1,3-bis-(4-fluoro-phenyl)-1,3-propanedione 
• 456-22-4 4-Fluorobenzoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 77815-14-6 2-amino-4-(4-fluorophenyl)thiazole 
• 219540-15-5 5-bromo-2-(4-fluorophenyl)-7-(trifluoromethyl)quinoxaline 
• 1261073-23-7 8-bromo-2-(4-fluorophenyl)-6-(trifluoromethyl)quinoxaline 
• 1261073-22-6 2-(4-fluorophenyl)-7-(trifluoromethyl)quinoxaline 
• 1261073-21-5 2-(4-fluorophenyl)-6-(trifluoromethyl)quinoxaline 
• 1234565-14-0 1-(4-fluorophenyl)-2-(morpholin-4-yl)-2-oxoethanone 
• 128400-42-0 S-[2-(4-fluorophenyl)-2-oxoethyl]-O-ethyl dithiocarbonate 

Relevant academic research and scientific papers

Practical Application of the Aqueous 'Sulfonyl-Azide-Free' (SAFE) Diazo Transfer Protocol to Less α-C-H Acidic Ketones and Esters

The earlier described 'sulfonyl-Azide-free' ('SAFE') protocol for diazo transfer to CH-Acidic 1,3-dicarbonyl compounds (and their similarly activated congeners) has been extended to the less reactive monocarbonyl substrates, which previously required a se

Rhodium-mediated 18F-oxyfluorination of diazoketones using a fluorine-18-containing hypervalent iodine reagent

Geminal 18F-oxyfluorination of diazoketones was performed in the presence of rhodium mediators. The reactions were performed using a hypervalent iodine-based [18F]fluoro-benziodoxole reagent. By this methodology various α-[18/s

Phosphoric Acid Catalyzed [4 + 1]-Cycloannulation Reaction of ortho-Quinone Methides and Diazoketones: Catalytic, Enantioselective Access toward cis-2,3-Dihydrobenzofurans

A highly straightforward route to enantiomerically highly enriched cis-2,3-dihydrobenzofurans has been achieved via addition of α-diazocarbonyl compounds to in situ generated o-QMs catalyzed by a chiral Br?nsted acid. This catalytic strategy provides a direct access to 2,3-dihydrobenzofurans in high yields and with up to 91:9 dr and 99:1 er at ambient temperature. Moreover, a unique phenonium-type rearrangement accounts for product formation with an inverted 2,3-substitution pattern.

Tandem Synthesis of α-Diazoketones from 1,3-Diketones

A highly efficient synthesis of α-diazoketone was achieved by simply stirring the mixture of 1,3-diketone, TsN3, and MeNH2 in EtOH. It was a tandem reaction including a novel primary amine-catalyzed Regitz diazo transfer of 1,3-diket

An efficient PEG-400 mediated catalyst free green synthesis of 2-amino-thiazoles from α-diazoketones and thiourea

A simple and efficient method has been developed for the synthesis of 2-aminothiazoles from α-diazoketones using PEG-400 solvent system. This novel synthetic approach involves the reaction between thiourea and α-diazoketones in PEG-400 at 100 °C to yield the corresponding 2-aminothiazoles in good yields. The method is simple, rapid and generates thiazole derivatives in excellent yields without the use of any catalysts. This green protocol can be utilized for fast synthesis of various 2-aminothiazoles in good yields. [Figure not available: see fulltext.]

SAR exploration at the C-3 position of tetrahydro-β-carboline sstr3 antagonists

MK-4256, a tetrahydro-β-carboline sstr3 antagonist, was discontinued due to a cardiovascular (CV) adverse effect observed in dogs. Additional investigations revealed that the CV liability (QTc prolongation) was caused by the hERG off-target activity of MK-4256 and was not due to sstr3 antagonism. In this Letter, we describe our extensive SAR effort at the C3 position of the tetrahydro-β-carboline structure. This effort resulted in identification of 5-fluoro-pyridin-2-yl as the optimal substituent on the imidazole ring to balance sstr3 activity and the hERG off-target liability.

Safe and reliable synthesis of diazoketones and quinoxalines in a continuous flow reactor

A flow method for the synthesis of aliphatic and aromatic diazoketones from acyl chloride precursors has been developed and used to prepare quinoxalines in a multistep sequence without isolation of the potentially explosive diazoketone. The protocol showcases an efficient in-line purification using supported scavengers with time-saving and safety benefits and in particular a reduction in the operator's exposure to carcinogenic phenylenediamines.

First example of the coupling of α-diazoketones with thiourea: a novel route for the synthesis of 2-aminothiazoles

α-Diazoketones undergo smooth coupling with thiourea in the presence of 10 mol % of copper(II) triflate to produce the corresponding 2-aminothiazoles in excellent yields with high selectivity. The use of copper(II) triflate makes this method simple, convenient and practical. This method works well with both aryl and alkyl diazoketones to furnish a wide range of 2-aminothiazoles.

Diazoaldehyde Chemistry. Part 1. Transdiazotization of Acylacetaldehydes in Neutral-to-Acidic Medium. A Direct Approach to the Synthesis of α-Diazo-β-oxoaldehydes

First ever non-deformylating transdiazotization of acylacetaldehydes was achieved: the reactions of 2-azido-1-ethylpyridinium tetrafluoroborate (4) with acylacetaldehydes 3 proceeded partially without deformylation to yield 16 new α-diazo-β-oxoaldehydes 1 along with diazomethyl ketones 2, especially in the presence of NaOAc (Scheme 1, Tables 1 and 2).The product distribution was substituent-dependent and could be correlated quantitatively.This new diazotization reaction appears as an alternative, direct, and more general method for the synthesis of these diazooxoaldehydes. α-Oxocycloalkanecarbaldehydes 5 gave only traces (if any) of α-diazocycloalkanones 7, and rearrangement products 6 were isolated (Scheme 2).Mechanisms of the reactions are discussed (Schemes 4 and 5).