76246-93-0Relevant academic research and scientific papers
Development of New Molecular Entities as Potent Antifungal Agents: Synthesis of Substituted 1,2,3-Triazoles
Jeshma, K.,Kumar, A. Kishore,Ramesh, G.,Sunitha, V.
, p. 2546 - 2553 (2022/01/22)
Abstract: A series of novel 1,2,3-triazoles (8a–8m) were synthesized usingclick chemistry in excellent yields and were characterized by IR, NMR, MASSspectroscopy and elemental analysis. The final compounds 8a–8m were assessed for theirantifungal activity. Among the compounds tested 8h, 8i, 8b, and 8e demonstrated potentantifungal activity where as compounds 8j,8d, 8l,and 8f were exhibited good antifungal activityagainst tested fungal strains compared to the reference drug Nystatin.
Proximity- and chelation-induced SNAr 1,4-aromatic ortho-substitution of ortho-methoxyphenyl 2-alkyl ketones
Grelier, Gwendal,Chénard, Etienne,Büschleb, Martin,Hanessian, Stephen
supporting information, p. 1091 - 1100 (2015/04/14)
The direct displacement of an o-methoxy group in o-methoxyaryl ketones with aryl, alkyl, and alkenyl Grignard reagents to provide a series of o-substituted ketones is described. Application of this reaction to the synthesis of a C-methyl analogue of a cyc
Design and synthesis of some pyrazole derivatives of expected anti-inflammatory and analgesic activities
Abd-El Gawad, Nagwa M.,Hassan, Ghaneya S.,Georgey, Hanan Hanna
experimental part, p. 983 - 994 (2012/07/31)
Design and synthesis of some pyrazole derivatives 4-11 of expected anti-inflammatory and analgesic activities. In addition, docking of the tested compounds into cyclooxygenase II using (MOE) was performed to rationalize the obtained biological results and their mechanism of action. The structures of the new compounds were elucidated by spectral and elemental analyses. All the newly synthesized compounds were evaluated for their anti-inflammatory activity using the carrageenan-induced rat paw edema method. Analgesic activity of the target compounds was measured using the p-benzoquinone writhing-induced method, and their ability to induce gastric toxicity was also evaluated. Results showed that the newly synthesized compounds exhibited weak to good activities compared to ibuprofen and celecoxib as reference drugs. Some compounds, such 4a and 11b exhibited significant anti-inflammatory activity with gastric ulcerogenic potential less than that of ibuprofen. Results of the analgesic activity showed that compounds possessing good anti-inflammatory activity showed also good analgesic. Substitution of pyrazole ring with at least one aryl moiety was found to be essential for anti-inflammatory and analgesic activities. Free NH (of pyrazole ring) and/or acidic group (COOH) will improve the anti-inflammatory activity. Springer Science+Business Media, LLC 2011.
Scandium triflate-catalyzed intramolecular Friedel-Crafts acylation with Meldrum's acids: insight into the mechanism
Fillion, Eric,Fishlock, Dan
experimental part, p. 6682 - 6695 (2011/02/26)
The intramolecular Friedel-Crafts acylation of arenes with Meldrum's acid derivatives catalyzed by Sc(OTf)3 was reported as a mild and general entry into functionalized 1-indanones. Mechanistic investigations were undertaken to determine the rate-determining step in the acylation sequence using Meldrum's acid, as well as to examine the role of the Lewis acid catalyst. Enolizable Meldrum's acid derivatives react via an acyl ketene intermediate under thermal conditions, while quaternized Meldrum's acid derivatives are thermally stable and only act as effective Friedel-Crafts acylating agents in the presence of a Lewis acid catalyst. The acylation was postulated to proceed through direct acylation of a Lewis acid-activated carbonyl. In the catalytic Friedel-Crafts acylation of Meldrum's acids, triflic acid appeared to be the active catalytic species, with Sc(OTf)3 serving as a very mild and convenient reagent for its delivery.
A high speed parallel synthesis of 1,2-diaryl-1-ethanones via a clean-chemistry C-C bond formation reaction
Veeramaneni, Venugopal Rao,Pal, Manojit,Yeleswarapu, Koteswar Rao
, p. 3283 - 3290 (2007/10/03)
In this report, we describe the parallel as well as conventional synthesis of 1,2-diaryl-1-ethanones via environmentally benign acylation of arenes with in situ generated arylacetyl trifluoroacetates. A wide variety of arylacetic acids I participated in trifluoroacetic anhydride/phosphoric acid mediated C-C bond formation reaction when reacted with arenes of type II to give 1,2-diaryl-1-ethanones III in good to excellent yield. Under the solvent-free conditions these chemical transformations that normally require longer reaction time can be performed within minutes in good yield.
Modulation of lifetimes and diastereomeric discrimination in triplet- excited substituted butane-1,4-diones through intramolecular charge-transfer quenching
Moorthy,Monahan,Sunoj,Chandrasekhar,Bohne
, p. 3093 - 3103 (2007/10/03)
Triplet lifetimes have been determined for the diastereomers of a broad set of butane-1,4-dione derivatives (1-3). A remarkable dependence of lifetimes on conformational preferences is revealed in that the lifetimes are shorter for the meso diastereomers of 1-3 than those for the racemic ones. The intramolecular β-phenyl quenching is promoted in the case of meso diastereomers by virtue of the gauche relationship between the excited carbonyl group and the β-aryl ring, while a distal arrangement in the lowest energy conformation (H-anti) in racemic diastereomers prevents such a deactivation. The involvement of charge transfer in the intramolecular β- phenyl quenching is suggested by the correlation of the triplet lifetimes of the meso diastereomers of compounds 2 with the nature of the substituent on the β-phenyl rings. In the case of racemic diastereomers, p-methoxy substitution on the β-phenyl ring (2-OCH3, 3-OCH3) also led to a decrease of the triplet lifetimes when compared to those of the nonsubstituted compounds (2-H, 3-H). This shortening is accounted for by the deactivation of a small proportion of the excited molecules through β-phenyl quenching. In addition to the above factors, the lifetimes in the case of meso diastereomers can further be controlled by increasing the energy spacing between the T1 and T2 states, since β-phenyl quenching occurs from the latter for compounds 2 and 3. Through a rational conformational control, a surprisingly long triplet lifetime (300 ns) has been measured for the first time for a purely n,π* triplet-excited β-phenylpropiophenone dimer (1- rac).
A Facile Synthesis of α-Methyldesoxybenzoins Including Racemates of Natural Angolensin, 2-O-Methylangolensin and 4-O-Methylangolensin
Jain, A. C.,Paliwal, Poonam
, p. 985 - 988 (2007/10/02)
Methylation of four different 2-hydroxydesoxybenzoins ( 1a, 1c, 1d, 1f) separately with methyl iodide in the presence of dry potassium carbonate and acetone at 35-40 deg C affords both C-methyl-(2a, 2d) and O-methyl-(1b, 1e) derivatives.However, 1a provid
The Chemistry of Nitrilium Salts. Part 3. The Importance of Triazinium Salts in Houben-Hoesch Reactions Catalyzed by Trifluoromethanesulphonic Acid
Amer, Muhannad I.,Booth, Brian L.,Noori, Ghazi F. M.,Proenca, M. Fernanda J. R. P.
, p. 1075 - 1082 (2007/10/02)
In the presence of trifluoromethanesulphonic (triflic) acid, isobutyronitrile reacts with anisole, 1,3-dimethoxybenzene, resorcinol, 1,3,5-trimethoxybenzene, and phloroglucinol at room temperature to give acylation products.A study of the reactions of acetonitrile and isobutyronitrile with triflic acid has shown that these modified Houben-Hoesch reactions occur by initial cyclotrimerization of the nitriles to 1,3,5-triazinium triflate salts followed by a slow reaction of the salts with the aromatic substrate.Support for this comes from the isolation of 2-(4-methoxyphenyl)-2,4,6-tri-isopropyl-1,2-dihydro-1,3,5-triazine from the reaction between anisole, triflic acid, and isobutyronitrile.Similar 1,2-dihydro-s-triazines and their salts have been prepared by reaction of trimethyl-s-triazinium triflate with 1,3-(MeO)2C6H4, and tri-isopropyl-s-triazinium triflate with 1,3-(RO)2C6H4 (R = H or Me) and 1,3,5-(MeO)3C6H3; these salts are easily hydrolyzed to the corresponding aromatic ketones.The salt +23SCF3 also reacts with o-phenylenediamine to give 2-methylbenzimidazolinium triflate in 83percent yield.Nitrilium salts NMe>+NMe>+3SCF3 at room temperature.
The Synthesis and Some Reactions of N-Methylnitrilium Trifluoromethanesulphonate Salts
Booth, Brian L.,Jibodu, Kehinde O.,Proenca, M. Fernanda
, p. 1151 - 1153 (2007/10/02)
N-Methylnitrilium trifluoromethanesulphonate (triflate) salts, prepared from nitriles and methyl triflate, have been shown to be useful reagents for the synthesis of aromatic ketimines and ketones, amidinium, imidate, and thioimidate salts, benzimidazoles, benzoxazoles, benzothiazoles, quinazolinones, and 1,2,4-triazolinium salts.
