33994-13-7Relevant academic research and scientific papers
Electrochemical Synthesis of 2-Bromoethyl and 2-Iodoethyl Ketones from Cyclopropanols
Barysevich, Maryia V.,Aniskevich, Yauhen M.,Hurski, Alaksiej L.
supporting information, p. 1934 - 1938 (2021/10/19)
A simple electrochemical protocol for the preparation of 2-bromoethyl- and 2-iodoethyl ketones from cyclopropanols and magnesium halides has been developed. The reaction proceeded with exclusive regioselectivity and without epimerization of the α-stereocenter in the products. We also showed that the synthesized diastereomerically pure 2-bromoethyl ketones undergo smooth copper and nickel-catalyzed alkylation, alkenylation, and arylations reactions.
Transformation of arenes into 3-arylpyrazoles and 3-arylisoxazolines with β-bromopropionyl chloride, hydrazine, and hydroxylamine
Yamamoto, Takahiro,Togo, Hideo
, (2020/01/31)
Successive treatment of arenes with β-bromopropionyl chloride and AlCl3, followed by the reactions with hydrazines and Na2CO3, and then with MnO2 gave the corresponding 3-arylpyrazoles in one pot in good to moderate yields. The same successive treatment of arenes with β-bromopropionyl chloride and AlCl3, followed by the reactions with hydroxylamine and KF gave the corresponding 3-arylisoxazolines in one pot in good to moderate yields.
Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones
An, Sejin,Moon, Da Yoon,Park, Bong Ser
, p. 6922 - 6928 (2018/10/24)
Photolysis of α-bromopropiophenones in acetonitrile results in formation of β-bromopropiophenones with good product selectivity, which can be coined as 1,2-Br shift reaction. The product selectivity increases when the reaction is done in neat or solid state, where only the 1,2-Br shift product is formed in some cases. The reaction is suggested to proceed by C–Br bond homolysis to give a radical pair, followed by disproportionation and conjugate addition of HBr to the α,β-unsaturated ketone intermediate. When the unsaturated intermediate is stabilized by an extra conjugation, the reaction stops at the stage, in which the unsaturated ketone becomes a major product. The synthetic method described in this research fits in a category of eco-friendly organic synthesis nicely since the reaction does not use volatile organic solvents and any other additives such as acid, base or metal catalysts, etc. Besides, the method fits into perfect atom economy, which does not give any side products. The synthetic method should find much advantage over other alternative methods to obtain β-bromo carbonyl compounds.
A gold-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade: Syntheses of medium-sized heterocycles
Sun, Yin-Wei,Tang, Xiang-Ying,Shi, Min
supporting information, p. 13937 - 13940 (2015/09/07)
The synthesis of medium-sized heterocycles possessing a trans double bond is still a challenge. Herein, gold(I)-catalyzed 1,2-acyloxy migration/intramolecular cyclopropanation/ring enlargement cascade reaction of furans has been developed, providing highly efficient access to ten- and eleven-membered heterocycles with a broad substrate scope under mild reaction conditions. The reaction outcome features high chemoselectivity at the C5-position of furan. Moreover, a trans-double bond was embodied in the medium ring system.
Anodic cyclization of dimethyl 2-(3-Oxo-3-arylpropyl) malonates into the corresponding dimethyl 2-aroylcyclopropane-1,1-dicarboxylates
Okimoto, Mitsuhiro,Yamamori, Haruki,Ohashi, Kousuke,Hoshi, Masayuki,Yoshida, Takashi
, p. 1568 - 1572 (2013/08/23)
A variety of dimethyl 2-(3-oxo-3-arylpropyl)malonates were electrooxidized in methanol, in the presence of potassium iodide and a base or a neutral salt, to give the corresponding cyclized dimethyl 2-aroylcyclopropane-1,1- dicarboxylates in moderate to good yields. The reactions were carried out under extremely mild reaction conditions, in which the optimal amount of electrolytic current varied from 2.12-2.41 F·mol-1 depending on the substrates. The reaction presumably proceeds via a two-electron oxidation process, in which iodide ions play an important role as the electron carrier between the anode and the substrate. Georg Thieme Verlag Stuttgart. New York.
Azido carbonyl compounds as DNA cleaving agents
Chowdhury, Nilanjana,Dutta, Sansa,Karthick,Anoop, Anakuthil,Dasgupta, Swagata,Pradeep Singh
, p. 25 - 34 (2012/11/07)
Irradiation of azido carbonyl compounds using UV light (≥310 nm) produced triplet alkyl nitrenes and aroyl radicals, which resulted in efficient cleavage of single strand DNA at pH 7.0. DNA cleaving ability of azido carbonyl compounds was found to be dependent on its concentration and substituents on its aromatic ring. Further, newly synthesized naphthalene based azido carbonyl compounds showed DNA cleavage ability at longer wavelength of UV light (≥350 nm) and also binding studies revealed that they bind to ct-DNA by weak intercalation mode.
Spiro-hydantoin compounds useful as anti-inflammatory agents
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Page/Page column 36, (2008/06/13)
Compounds having the formula (I), and pharmaceutically-acceptable salts, hydrates, enantiomers, and diastereomers, and prodrugs thereof, are useful as inhibitors of LFA-1/ICAM and as anti-inflammatory agents, wherein L and K are O or S; Z is N or CR4b; Ar is an optionally-substituted aryl or heteroaryl; G is a linker attached to T or M or is absent; J, M and T are selected to define a three to six membered saturated or partially unsaturated non-aromatic ring; and R2 R4a, R4b, and R4c are as defined in the specification.
