2-(3-Nitrophenyl)-2-oxazoline

Decken, Andreas; Botelho, Laura; Sadowy, Amber L.; Yadav, Pravesh; Gossage, Robert A.

doi:10.1107/s1600536806045454

Cited by 6 publications

(3 citation statements)

References 20 publications

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“…Single crystals were obtained by slow evaporation of the ethyl acetate solution. In the title compound bond lengths and angles in the oxazoline ring are comparable with those in related structures [11][12][13][14][15][16] …”

Section: Discussionsupporting

confidence: 67%

“…This is contray to the findings in the related structure [13] which resume almost coplanar relation between oxazoline and 2-aryl rings and probably is as aresult of steric interactions due to the presence of cholorine substituent at the ortho position of 2-aryl ring. Anti relation of phenyl and benzoyl groups at 4and 5positions, respectively, is evident with torsion angles N1−C2− C3−C16 …”

Section: Discussioncontrasting

confidence: 64%

“…In the assignment of the right isomer, spectral data (IR, NMR and MS) were not conclusive therefore, X-ray structure analysis was conducted on the reaction product which established the formation of the title regioisomer. Despite the extensive studies on 2-oxazoline ring, only few metal-free species have been examined by X-ray diffraction methods [11][12][13][14][15][16][17][18]. Single crystals were obtained by slow evaporation of the ethyl acetate solution.…”

Section: Discussionmentioning

confidence: 99%

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Crystal structure of 5-benzoyl-2-(2-chlorophenyl)-4-phenyl-2-oxazoline, C22H16ClNO2

Mamaghani¹,

Tabatabaeian²,

Samimi³

2008

Zeitschrift Für Kristallographie - New Crystal Structures

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C 22 H 16 ClNO 2 ,monoclinic, P12 1 /n1(no. 14), a =10.6113(7) Å, b =9.6680(6) Å, c =17.176(1) Å, b =92.910(1)°, V =1759.8 Å 3 , Z =4,Rgt(F) =0.045, wRref(F 2 ) =0.111, T =100 K. Source of materialAs olution of trans-2-bezoyl-N-(2-chlorobenzoyl)-3-phenylaziridine (0.361 g, 1.0 mmol) in CH 3CN (15 ml) and NaI (0.2 mmol) was stirred at 50°C for 6h ours. Then the mixture was rinsed twice with water, the organic layer was separated and dried with anhydrous Na 2 SO 4 .E vaporation of the solvent under reduced pressure and subsequent purification of the residue by column chromatography (silica gel, EtOAc/hexane: 1/4) provided 5-benzoyl-2-(2-chlorophenyl)-4-phenyl-2-oxazoline (0.325 g, 0.9 mmol) in 90 %yield, mp =125 -127°C. Elemental analysis -found: C, 73.12 %; H, 4.40 %; N, 3.77 %; calculated for C 22 H 16 ClNO 2 :C,73.08 %; H, 4.47 %; N, 3.87 %. Melting points were measured on aBuchi melting point B-540 instrument and are uncorrected. Elemental analyses were made by a Carlo-Erba EA1110CNNO-S analyzer. Experimental detailsThe H(C) atom positions were calculated. All hydrogen atoms were refined in isotropic approximatiom in riding model with the U iso(H) parameters equal to 1.2 Ueq(Ci), where Ueq(Ci) are the equivalent thermal parameters of the carbon atoms to which corresponding Hatoms are bonded. DiscussionThe oxazolines group is an important functionality in synthetic organic chemistry [1]. 2-Substituted 2-oxazolines as important heterocyclic intermediates and precursors of great variety of carboxylic acid derivatives and many biologically active compounds and ligands in amultitude of metal-catalyzed reactions, have attracted strong attentions [2-6]. Substituted oxazoline derivatives prepared stereospecifically were used in the synthesis of naturally occurring non-proteinogenic β-hydroxy-a-amino acids [7] and as starting material in the synthesis of the neurotrophic factor Lactacystin [8,9]. Several synthetic methods have been described for the synthesis of oxazolines. One interesting method is the ring expansion of N-ketoaziridines induced by iodide [10]. In the iodide isomerization of trans-2-bezoyl-N-(2-chlorobenzoyl)-3-phenylaziridine, formation of two regio-isomers is possible, namely 5-benzoyl-2-(2-chlorophenyl)-4-phenyl-2-oxazoline (1) and 4-benzoyl-2-(2-chlorophenyl)-5-phenyl-2-oxazoline. In the assignment of the right isomer, spectral data (IR, NMR and MS) were not conclusive therefore, X-ray structure analysis was conducted on the reaction product which established the formation of the title regioisomer. Despite the extensive studies on 2-oxazoline ring, only few metal-free species have been examined by X-ray diffraction methods [11][12][13][14][15][16][17][18]. Single crystals were obtained by slow evaporation of the ethyl acetate solution. In the title compound bond lengths and angles in the oxazoline ring are comparable with those in related structures [11][12][13][14][15][16]

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