20651-76-7Relevant articles and documents
A Systematic Study on the Synthesis of n-Butyl Substituted 8-Aminoquinolines
Koseoglu, Ahmet,Gul, Turan,Acar, Ali Ersin
, p. 263 - 270 (2016/02/10)
(Chemical Equation Presented) A systematic study on the synthesis of 8-aminoquinoline derivatives with an n-butyl group at each alternate position of the quinoline ring was carried out. Skraup Reaction and its Doebner-von Miller variation were used to obtain most of the quinoline ring except for the 2-butyl-8-aminoquinolines and 4-butyl-8-aminoquinolines where the commercially available methylquinoline derivatives were used as precursors. The structures of the synthesized compounds were characterized by FTIR, 1H-NMR, COSY, 13C-NMR and HRMS spectra.
Regioselective mononitration of aromatic compounds with N2O5 by acidic ionic liquids via continuous flow microreactor
Liu, Jianhua,Li, Bindong,Wang, Huan
, p. 513 - 516 (2016/01/20)
We employed N2O5 as highly active nitrating reagents and a host of acidic ionic liquid as catalysts in these reactions which were conducted in a continuous flow microreactor. When we utilized PEG400-DAIL as catalysts, the conversion of toluene was increased to 95.5 % and the yield of mononitration product (o/p ratio reached 1.10) significantly improved to 99 %, meanwhile the reaction time was drastically shortened to 1/120 of the conventional reactor. Nitration in ionic liquids was surveyed using a host of aromatic substrates with similar reactivity. The ionic liquid recycling procedures had also been devised.
Alkylboronic esters from copper-catalyzed borylation of primary and secondary alkyl halides and pseudohalides
Yang, Chu-Ting,Zhang, Zhen-Qi,Tajuddin, Hazmi,Wu, Chen-Cheng,Liang, Jun,Liu, Jing-Hui,Fu, Yao,Czyzewska, Maria,Steel, Patrick G.,Marder, Todd B.,Liu, Lei
supporting information; experimental part, p. 528 - 532 (2012/02/04)
Easy access: An unprecedented copper-catalyzed cross-coupling reaction of the title compounds with diboron reagents is described (see scheme; Ts=4-toluenesulfonyl). This reaction can be used to prepare both primary and secondary alkylboronic esters having diverse structures and functional groups. The resulting products would be difficult to access by other means. Copyright
Palladium-catalyzed cross-coupling alkylation of arenediazonium o-benzenedisulfonimides
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
, p. 474 - 478 (2008/09/21)
Arenediazonium o-benzenedisulfonimides were reacted with tetramethyltin, tetrabutyltin or trialkylboranes. The reactions, carried out in the presence of palladium(II) derivatives as precatalysts, gave the methylation and alkylation products with good over
Nitration of alkylbenzenes in acid medium: Regioselectivity of the reaction and acidity of the medium
Krylov
, p. 1413 - 1418 (2007/10/03)
Isomer distribution in the nitration of toluene and its homologs with nitric acid in acid media (trifluoroacetic acid and solutions of sulfuric acid in acetic acid) is determined by the acidity of the medium, the degree of para substitution changing in parallel with the acidity. The ortholpara regioselectivity is governed by the polarity of the transition state. The sensitivity of the ortholpara ratio to variation of the acidity of the medium and reaction temperature is directly related to steric effects of the alkyl groups.
Nitration of Alkylbenzenes in Trifluoroacetic Acid
Krylov,Gvozdareva
, p. 1618 - 1623 (2007/10/03)
The substrate selectivity of alkylbenzene nitration with nitric acid in trifluoroacetic acid is controlled either by electronic or by steric effects of the substituents, depending the medium composition and temperature. The positional selectivity of this reaction is sterically controlled, even under electronic control of substrate selectivity.
Ozone-mediated nitration of phenylalkyl ethers, phenylacetic esters, and related compounds with nitrogen dioxide. the highest ortho substitution observed in the electrophilic nitration of arenes
Suzuki, Hitomi,Takeuchi, Toyomi,Mori, Tadashi
, p. 5944 - 5947 (2007/10/03)
By the combined action of ozonized oxygen and nitrogen dioxide (the kyodai-nitration), the title compounds were smoothly nitrated in dichloromethane at subzero degrees with hiigh ortho positional selectivity. Although the conventional nitration of phenylacetic acid and esters mainly produces m- and p-nitro derivatives, the present nitration offers a simple high-yield synthesis of o-nitro derivatives which are important as precursor in organic synthesis. The proportions of the ortho isomer in the nitration products from methyl 2-phenylethyl ether and methyl phenylacetate were 71 and 88%, respectively, the latter value being the highest ortho isomer proportion so far observed in the electrophilic aromatic nitration. The observed high ortho selectivity has been rationalized in terms of radical cation intermediate and six-membered cyclic transition state.
NITRATION OF ALKYLBENZENES WITH NITRIC ACID IN ORGANIC SOLVENTS. SUBSTRATE AND POSITION SELECTIVITY
Krylov, E. N.,Khromova, I. N.
, p. 2179 - 2186 (2007/10/02)
The substrate and position selectivity in the nitration of alkylbenzenes (with normal and iso C1-C4 alkyl groups) in organic solvents (protic and bipolar aprotic solvets) with and without sulfuric acid in the range of 25-75 deg C is determined mainly by the steric affect of the substituents.Nathan-Bacer substrate and position effects are observed.Linear correlations are found between the result of the orientation of the nitro group and the steric parameters of the substituets.The substrate selectivity varies inversely and the position selectivity varies directly with the latter.The sensitivity of the orientation to change in the geometry of the substituets varies directly with temperature.
