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Upstream product

• 13361-64-3 trimethyl(propargyl)silane 
• 109423-09-8 1,3,5-tris(4-fluorophenyl)-1,3,5-triazinane 
• 78-94-4 methyl vinyl ketone 
• 371-40-4 4-fluoroaniline 
• 491-35-0 C₆H₄NCH₂CHCCH₂ 
• 1060813-09-3 tert-butyl N-(4-fluoro-2-iodophenyl)carbamate 
• 1384466-93-6 C₁₅H₁₉FINO₃ 
• 1384466-94-7 C₁₅H₂₀FNO₃ 
• 391-77-5 4-Chloro-6-fluoroquinoline 
• 75-16-1 methylmagnesium bromide 
• 4652-27-1 4-methoxy-3-buten-2-one 
• 60144-53-8 N-(tert-butoxycarbonyl)-4-fluoroaniline 

Relevant academic research and scientific papers

Metal-Free Chemoselective Oxidation of 4-Methylquinolines into Quinoline-4-Carbaldehydes

A convenient protocol for the synthesis of quinoline-4-carbaldehydes via chemoselective oxidation of 4-methylquinolines using hypervalent iodine(III) reagents as oxidant is described. This method highlights metal-free and mild reaction conditions, nice yield, good functional group tolerance, and high chemoselectivity.

Efficient synthesis of substituted quinolines through intramolecular addition of aryl anion to carbonyl carbon

Substituted quinolines were synthesized in three steps from the Boc amides of substituted 2-iodoanilines and alkyl vinyl ketones. This method consists of (1) N-Michael addition of the Boc amide of 2-iodoaniline to alkyl vinyl ketone in the presence of Cs2CO3 in MeCN; (2) I-Mg exchange of the adduct with 3.5 equiv of i-PrMgCl·LiCl, and (3) acid-catalyzed reaction (excess AcCl in EtOH) of the resulting alcohol. Six examples are given with good yields.

Elemental fluorine Part 15. Selective direct fluorination of quinoline derivatives

Direct fluorination of various quinoline derivatives in acidic reaction media gives fluorinated quinoline products arising from electrophilic substitution processes.

Anti-mutagenic structural modification by fluorine-substitution in highly mutagenic 4-methylquinoline derivatives

We have previously shown that fluorine-substitution at position 3 of quinoline deprived this molecule of mutagenicity, possibly due to interference with the yield of its metabolically activated form, the 1,4-hydrated 2,3-epoxide (enamine epoxide), which is directly responsible for the mutagenic modification of DNA. To further explore the possibility of a method for anti-mutagenic modification of mutagens by fluorine-substitution, 4-methylquinoline (4-MeQ), the most mutagenic form of all the quinoline derivatives examined so far, was used as a target in the present study. Five mono- and di-fluorinated derivatives of 4-MeQ, 2-fluoro-4-methylquinoline (2-F-4-MeQ), 6-F-4-MeQ, 7-F-4-MeQ, 2,6-difluoro-4-methylquinoline (2,6-diF-4-MeQ), and 2,7-diF-4-MeQ, were subjected to analysis of their structure-mutagenicity relationships. The 2-fluorinated derivatives (2-F-4-MeQ, 2,6-diF-4-MeQ, and 2,7-diF-4-MeQ) were all non-mutagenic in the Ames test. 7-F-4-MeQ was as highly mutagenic as, and 6-F-4-MeQ was less mutagenic than non-fluorinated 4-MeQ. Metabolic studies were also conducted with 4-MeQ, 2-F-4-MeQ, 6-F-4-MeQ, and 7-F-4-MeQ, using a liver microsomal enzyme fraction prepared from the 3-methylcholanthrene-treated rat. The HPLC analytical data showed that, although the metabolic patterns (hydroxylation at 4-methyl group as a main metabolic pathway and 3-hydroxylation as a minor pathway) of these four F-MeQs were similar to one another, only the 3-hydroxy metabolite of 2-F-4-MeQ was not produced under the present experimental conditions employed. These results suggest that fluorine-substitution at position 2 of 4-MeQ inhibited the formation of the enamine epoxide in the pyridine moiety and deprived this molecule of mutagenicity as in the case of quinoline. Copyright (C) 2000 Elsevier Science B.V.

Addition of propargyltrimethylsilane to N-methyleneamine equivalents: Generation and electrophilic cyclization of vinylic carbocations

Lewis acid induced N-methyleneamine equivalents from N-(methoxymethyl)anilines or 1,3,5-triphenylhexahydro-1,3,5-triazines reacted with propargyltrimethylsilanes to give N-buta-2,3-dienylanilines, 4-methylene-1,2,3,4-tetrahydroquinolines and its oxidized product of 4-methylquinolines. These products came from branching reactions of the elimination and electrophilic aromatic substitution from the same vinylic carbocation intermediate.