71027-98-0Relevant academic research and scientific papers
Diastereoselective One-Pot Synthesis of Oxazolines Using Sulfur Ylides and Acyl Imines
Mehedi, Md Shafaat Al,Tepe, Jetze J.
, p. 7219 - 7226 (2019/06/14)
This work describes an extended version of the Corey-Chaykovsky reaction to access oxazolines using sulfur ylides and stable precursors of acyl imines. The reaction proceeds through a mixture of aziridines and oxazolines, which provides the trans-oxazolines following in situ Heine-type aziridine ring expansion upon treatment with BF3·OEt2. Following the same one-pot procedure, amidine imides react with the sulfur ylides to provide imidazolines.
Synthesis of some derivatives of 4,5-dihydrooxazoles
Piri, Farideh,Ghaforinia, Nastaran,Taghavi, Mohammad,Karimian, Ramin
scheme or table, p. 1403 - 1406 (2012/04/10)
Benzaldehyds with sodium amide in the presence of thiourea in tetrahydro furan at room temperature gave various 2,4,5-triphenyl-4,5-dihydrooxazoles. The thiourea-catalyzed condensation of the benzaldehyde yielded 2-amino-1,2- diphenylethanone. Reduction of 2-amino-1,2-diphenylethanone was performed with hydride from Cannizzaro reaction to give 2-amino-1,2-diphenylethanols. The 4,5-dihydrooxazole ring formation of the 2-amino-1,2-diphenylethanol and benzamide gave the desired 4,5-dihydrooxazole.
Copper-catalyzed oxidative desulfurization-promoted intramolecular cyclization of thioamides using molecular oxygen as an oxidant: An efficient route to five- To seven-membered nitrogen-containing heterocycles
Shibahara, Fumitoshi,Yoshida, Atsunori,Murai, Toshiaki
, p. 646 - 647 (2008/12/21)
Copper-catalyzed oxidative desulfurization-promoted intramolecular cyclization reactions of thioamides take place under neutral and mild conditions by using molecular oxygen as an oxidant. The process yields a wide variety of nitrogen-containing heterocyc
Stereoselective one-pot synthesis of oxazolines
Hajra, Saumen,Bar, Sukanta,Sinha, Debarshi,Maji, Biswajit
, p. 4320 - 4322 (2008/09/20)
(Chemical Equation Presented) Treatment of alkenes with NBS, a nitrile, NaHCO3 and water in the presence of Cu(OTf)2 or Zn(OTf)2 is reported to furnish oxazolines in one pot and good yields. The reaction is equally applica
Acid catalysed rearrangement of some N-acylaziridines
Besbes, Neji
, p. 313 - 318 (2007/10/03)
The reaction of N-acylaziridines 1 with concentrated sulfuric acid leads to the oxazolines 3 and/or amidoalcohols 4. The geometry of the aziridines 1 is discussed and an ionic mechanism is proposed.
A novel synthesis of imidazoles via the cycloaddition of nitrile ylides to their imidoyl chloride precursors
Groundwater, Paul W.,Garnett, Ian,Morton, Andrew J.,Sharif, Toqir,Coles, Simon J.,Hursthouse, Michael B.,Nyerges, Miklos,Anderson, Rosaleen J.,Bendell, David,McKillop, Alexander,Zhang, Weimin
, p. 2781 - 2787 (2007/10/03)
The synthesis of imidazoles via the cycloaddition of nitrile ylides to their imidoyl chloride precursors was presented. The nitrile ylides were prepared by the 1,3-dehydrochlorination of imidoyl chlorides. It was shown that the HOMO of the 'bent' nitrile ylide is heavily localized on the methane terminus and is compatible with protonation at this carbon in substituted nitrile ylides and with the regioisomers obtained in biomolecular nitrile ylide cycloadditions. The observed regiochemistry of the cycloaddition was rationalized by energy calculations on the frontier molecular orbitals of the reactants using semi-empirical methods.
Friedel-Crafts reactions of some N-acylaziridines: Oxazolines as intermediates
Mall,Buchholz,Stamm
, p. 377 - 380 (2007/10/02)
Without heat supply, AlCl3 and 3-substituted 1-acyl-2-phenylaziridines 1a,b, and 2b in benzene provided the respective Friedel-Crafts products 3a,b, and 4b (acylated 1-substituted 2,2-diphenylethylamines) which in part were further converted to 1,1,2,2-teraphenylethane (5). Oxazolines 6a,b, and 7b were also found. It is shown by means of 2,4,5-triphenyloxazoline 6b that oxazolines are intermediates for 3, 4, and 5. The uncommon heterolysis of these particular oxazolines is discussed.
Evolutions differentes de radicaux anions formes par voie chimique ou electrochimique
Archier-Jay, Danielle,Besbes, Neji,Laurent, Andre,Laurent, Eliane,Lesniak, Stanislaw,Tardivel, Robert
, p. 537 - 543 (2007/10/02)
Chemical and electrochemical reductions of N-aroylaziridines 1 are described and compared.The first step is a single electron transfer (1 +e -> 1-. -> 1'-.).But compounds obtained from 1'-. are depending on the method used way followed: chemical reduction of N-cinnamoylaziridine 1e provides pyrrolidone 10e; but oxazoline 11e is available by electrochemical reduction of the same starting material 1e.Counter ion seems responsible of these different results.In agreement with this hypothesis, it is shown that pyrrolidone 10e is obtained from 1j only in presence of a counter ion.
Reactions with Aziridines, 46 Ring Opening of Stilbene Imines by Thiophenolate
Mall, Thomas,Stamm, Helmut
, p. 1353 - 1356 (2007/10/02)
Ring opening by thiophenolate of cis-trans pair of stilbene imines proceeds stereospecifically irrespective of the kind of mono activation by the phenylsulfonyl group (1), by the benzoyl group (2), or by protonation of the aziridine base (3).In accordance
A Reinvestigation of the Pictet-Gams Isoquinoline Synthesis. Part 2. Formation of Rearranged Isoquinolines: the Δ2-Oxazoline-Isoquinoline Transformation
Ardabilchi, Nasser,Fitton, Alan O.,Hadi, A. Hamid b. A.,Thompson, J. Robin
, p. 1710 - 1725 (2007/10/02)
Cyclisation of a series of 2-substituted 2-acylamino-1-arylalkan-1-ols using phosphorus pentaoxide in refluxing decalin is shown to lead to rearranged, i.e. 4-substituted, isoquinolines in addition to the anticipated 3-substituted isomers.The products arise largely via 5-phenyl-Δ2-oxazoline intermediates and the formation of the rearranged isoquionolines from these intermediates is fully discussed.The pathway is not substantially altered when 2-benzamido-1-methoxy-1-phenylalkanes are cyclised.
