- The α-chlorination of aryl methyl ketones under aerobic oxidative conditions
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The novel reaction system air/ammonium nitrate/iodine/hydrochloric acid [air/NH4NO3(cat.)/I2(cat.)/HCl] is introduced as a simple, safe, cheap, efficient and regioselective mediator for the α-chlorination of aryl, heteroaryl and alkyl methyl ketones under aerobic oxidative conditions. The inventive use of a catalytic amount of iodine enabled the moderate to quantitative, regioselective chlorination of a comprehensive scope of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents, some of which possess declared potential biological and pharmaceutical activity. Air oxygen under a slight overpressure plays the role of the terminal oxidant catalytically activated by redox cycles of nitrogen oxides released from the catalytic amount of ammonium nitrate (NH4NO3) under acidic conditions of hydrochloric acid (HCl) and co-catalyzed by elemental iodine (I2), which was found to be essential for the high efficiency of the reaction system.
- Prebil, Rok,Stavber, Stojan
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supporting information
p. 1266 - 1274
(2014/05/06)
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- Solvent free synthesis of 2-acylpyrroles and its derivatives catalysed by reuseable zinc oxide
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A highly efficient procedure for preparing 2-acylpyrroles and its derivatives is described. The products were obtained through regioselective Friedel-Crafts reactions of pyrroles and its derivatives with alkyl or aryl acid chlorides catalysed by zinc oxide under solvent-free conditions. This method has the advantages of green chemistry, operational simplicity, solvent-free conditions, and recoverable catalyst.
- Zhang, Shuguang,Feng, Chengliang,Cai, Jin,Chen, Junqing,Hu, Huayou,Ji, Min
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p. 480 - 482
(2013/09/12)
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- Enantioselective synthesis of heteroaromatic epoxyketones under phase-transfer catalysis using D-glucose- and D-mannose-based crown ethers
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Heteroaromatic epoxyketones have been synthesized in an asymmetric Darzens condensation of 2-chloroacetylfuran or 2- and 3-chloroacetylthiophene with aromatic aldehydes and in the enantioselective epoxidation of α,β-enones with an N-methylpyrrole unit, in
- Rapi, Zsolt,Szabo, Tamas,Keglevich, Gyoergy,Szxoellosy, Aron,Drahos, Laszlo,Bako, Peter
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body text
p. 1189 - 1196
(2011/10/19)
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- Spectroscopic and theoretical studies on some new pyrrol-2-yl-chloromethyl ketones
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A novel series of pyrrole-2-yl chloromethyl ketones were synthesized and studied by FT-IR, 1H, 13C NMR spectroscopy and DFT calculations at the B3LYP/6-311++G(d,p) level of approximation. Two stable conformations were detected in solution: s-cis and s-trans forms where the C=O group is located on the same side or the opposite side of N-H group, respectively. The conformational stability of these molecules is governed mainly by intermolecular hydrogen bonding interactions. The strength of hydrogen bonds was evaluated on the basis of 1H chemical shift and infrared red shift ΔνN-H of the stretching vibration of N-H proton donating bonds. The quantum theory of 'atoms in molecules' as well as the natural bond orbital method were applied to characterize hydrogen bonding interactions. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2010.
- Dubis, Alina T.,Domagala, Malgorzata,Grabowski, Slawomir J.
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experimental part
p. 556 - 566
(2010/06/13)
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- Novel building blocks: 1-Aryl-2-chloro-1-ethoxyethenes - Preparations and transformations
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We described here a simple method for the preparation of 1-aryl-2-chloro-1-ethoxyethenes 2a-u, which are prodrugs for Alzheimer's disease, by the reaction of dichloroacetaldehyde diethyl acetal with various aryl and alkenyllithium compounds in high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
- Yoshimatsu, Mitsuhiro,Sakai, Miho,Moriura, Eri
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p. 498 - 507
(2008/02/06)
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- Ytterbium (III) trifluoromethanesulfonate catalysed Friedel-Crafts acylation of 1-methylpyrrole in ionic liquid
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In the presence of a catalytic amount of ytterbium (III) trifluoromethanesulfonate [Yb(OTf)3], 1-methylpyrrole can easily react with acyl chlorides in an ionic liquid [bpy][BF4](bpy=1- butylpyridine) to form corresponding ketones in satisfactory yield. The recyclability of the ionic liquid/catalyst system is demonstrated.
- Su, Weike,Wu, Chunlei,Su, Hao
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- Design, synthesis, and biological activities of pyrrolylethanoneamine derivatives, a novel class of monoamine oxidases inhibitors
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Pyrrolylethanoneamines 1-12, 18-23 and related amino alcohols 13-15, 24-27 were synthesized and tested against monoamine oxidases A and B (MAO-A and MAO-B) enzymes. In general, aminoketones 1-12, 18-23 were found to be potent and selective MAO-A inhibitor
- Di Santo, Roberto,Costi, Roberta,Roux, Alessandra,Artico, Marino,Befani, Olivia,Meninno, Tiziana,Agostinelli, Enzo,Palmegiani, Paola,Turini, Paola,Cirilli, Roberto,Ferretti, Rosella,Gallinella, Bruno,La Torre, Francesco
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p. 4220 - 4223
(2007/10/03)
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- Aroyl aminoacyl pyrroles for use in the treatment of neuropathic pain
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Aroyl aminoacyl pyrroles are pharmaceutically useful in treating neuropathic pain, which includes utility for the treatment of neuropathic pain.
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Page column 21
(2008/06/13)
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- Aroyl aminoacyl pyrroles for use in the treatment of neuropathic pain
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Aroyl aminoacyl pyrroles are pharmaceutically useful in treating neuropathic pain, which includes utility for the treatment of neuropathic pain.
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- Anti-convulsant aroyl aminoacylpyrroles
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Aroyl aminoacyl pyrroles are pharmaceutically useful as anti-convulsants, which includes utility for the treatment of epilepsy.
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- Selective α-Chlorination of Acetylpyrroles
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Reaction of acetylpyrroles with benzyltrimethylammonium dichloroiodate in tetrahydrofuran solution leads to the corresponding α-chloro derivatives with high selectivity and good yields.
- Croce, Piero Dalla,Ferraccioli, Rafaella,Ritieni, Alberto
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p. 212 - 213
(2007/10/02)
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- Direct Vilsmeier-Haack Chloroacetylation of Pyrroles
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Reaction of pyrroles with N,N-dimethyl-2-chloroacetamide in the presence of phosphorus oxychloride leads to a mixture of 2- and 3-chloroacetylpyrroles, which can be separated by chromatography.
- Croce, Piero Dalla,Rosa, Concetta La,Ritieni, Alberto
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p. 783 - 784
(2007/10/02)
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