Conversion of 2-isoxazolines into aziridines by lithium aluminum hydride reduction

Reduction of Some Alkylisoxazoles with Lithium Aluminum Hydride

“…data with those of Kotera et al (1) and a consideration of the likely mechanisms involved. In the case of hydroxyaziridine formation, hydride attack apparently occurs at C, followed by C, -+ N cyclization and N-0 bond fission.…”

“…Whereas previous reports (3-6) described the formation of only the 1,3-amino alcohol, Kotera et al (1) obtained significant yields (20-80%) of aziridine as well as the corresponding amino alcohol. The relative proportion of aziridine to amino alcohol was found to be solvent dependant (1). The stereochemistry of the substituted aziridines obtained was deduced from n.m.r.…”

“…The reduction of isoxazolines with lithium aluminum hydride (LAH) has been described by Kotera et al (1,2). Whereas previous reports (3-6) described the formation of only the 1,3-amino alcohol, Kotera et al (1) obtained significant yields (20-80%) of aziridine as well as the corresponding amino alcohol.…”

The preparation of 3,3a,4,5-tetrahydronaphth[1,2-c]isoxazoles from dilithiated 1-tetralone oxime and select aromatic aldehydes

“…This compound was prepared in 33 % yield (1.68 g), mp 144-146°(ethanol), using the general procedure for the condensationcyclization of dilithiated 1-tetralone oxime and 2,4,5trimethoxybenzaldehyde: IR 1613 cm -1 ; 1 H NMR (deuteriochloroform): δ (ppm) 1.66-1.74 (m, 1H), 2.09-2.14 (m, 1H), 2.70 (s broad, 2H), 3.09-3.19 (m, 1H), 3.55-3.66 (m, 9H), 5.31 (d, 1H, J = 12.3 Hz), 6.30 (s, 1H), 6.61-7.00 (m, 4H), and 7.74 (d,1H,J = 7.5 Hz). 13 C NMR (deuteriochloroform): δ (ppm) 27.2, 29.…”

1-[2-(4-Nitrophenyl)-5-(5-phenyl-1,2-oxazol-3-yl)-1,2,3,4-tetrahydroquinolin-4-yl]pyrrolidin-2-one

“…For details of nitrogen-containing heterocyclic compounds, see: Sankaran et al (2010) and for their pharmacological activity, see: Shi et al (2008); Lunniss et al (2009); He et al (2005); Eswaran et al (2010). For reactions of isoxazoles, see: Taldone et al (2008); Narlawar et al (2008); Velaparthi et al (2008); Rizzi et al (2008); Lautens & Roy (2000); Broggini et al (2005); Kotera et al (1970). For applications of compounds possessing the quinoline system as drugs and pharmaceuticals, see: Kalita et al (2006).…”