Oxazolines, synthesis

R. Tralli, C. Troisi, L. Lithiation of 2-(l-chloro-efhyl)-2-oxazolines synthesis of substituted oxazolinyloxiranes and oxazolinylaziridines. Synthesis 2001,2299-2306. 

Christova, D., Velichkova, R., and Goethals, E.J. (1997) Bis-macromonomeis of 2-alkyl-2-oxazolines - synthesis and polymerization. Macromolecular Rapid Communications, 18,1067 1073. 

The reaction of difunctional nucleophiles with alkyl isocyanides under the influence of silver cyanide as catalyst has been described in an earlier section on imidazoles an example of the use of this simple approach in an oxazoline synthesis is shown in Scheme 107.169... 

Fig. 12 Oxazoline synthesis with the acid-derived amide acting as nucleophile...

Ferrocenyl ligands, via zinc reagents, 9, 120 Ferrocenylmethyl phosphonium salts, with gold(I), 2, 274 Ferrocenylmonophosphine, in styrene asymmetric hydrosilylation, 10, 817 Ferrocenyl oxazolines, synthesis, 6, 202 Ferrocenylphosphines with chromium carbonyls, 5, 219 in 1,3-diene asymmetric hydrosilylation, 10, 824-826 preparation, 6, 197 various complexes, 6, 201 Ferrocenylselenolates, preparation, 6, 188 Ferrocenyl-substituted anthracenes, preparation, 6, 189 Ferrocenyl terpyridyl compounds, phenyl-spaced, preparation 6, 188 Ferrocifens... 

In its utilization of acetonitrile, the oxazoline synthesis shown in Scheme 56 resembles a Ritter reaction.The procedure is convenient, but yields are variable the pyrolysis gives starting alkene plus acetamide as by-products. Another oxazoline synthesis and subsequent conversion to a cif-amino alcohol is discussed later (Scheme 85). A recent y-hydroxy-a-amino acid synthesis incorporates the following type of transformation (Scheme 57).If a three-day equilibration with anhydrous HBr was introduced iMtween stages i and ii, almost pure trans product was obtained. The paper has many usefol references. Yet another modified Ritter reaction is shown in Scheme 58. ... 

Zurabyan, S E, Volosyuk, T P, Khorlin, A J, Oxazoline synthesis of l,2-tranj-2-acetamido-2-deoxyglycosides, Carbohydr. Res., 9, 215-220, 1969. 

Meyers and Hoyer have shown that the Ph P/CClj /Etmethod for oxazoline synthesis from acids and amino-alcohols proceeds with inversion at the carbinol centre, contrary to what was previously thought. Oxazolines can also be synthesized by the ZnCl2 ... 

Chung YM, Raman B, Ahn KH (2006) Phenol-containing bis(oxazolines) synthesis and fluorescence sensing of amines. Tetrahedron 62 11645-11651... 

The novel concept of elaboration of unactivated olefins by nucleophiles has been reported. Nucleophilic attack is initiated by reaction of the olefin with dimethyl(tnethylthio)sulphonium fluoroborate (4) and, in conjunction with nitrogen nucleophiles, a high degree of regiocontrol is observed in an azasul-phenylation reaction (Scheme 7), the products of which not only permit an overall olefin amination, but also an oxazoline synthesis, a m-hydroxyamination, and an aziridine synthesis. The analogous selenium reagent, dimethyl(phenyl-seleno)sulphonium fluoroborate, p-phenylselenates a variety of anilines in moderate yield. ... 

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