Α-amino Oximes Research Articles

Synthesis of glycidyl ethers derived from terpene α-amino oximes and β-substituted alcohols on their basis

3-Carene, α-pinene, and limonene α-(dimethylamino)oximes were converted to glycidyl ethers at the oxime hydroxyl. The compounds obtained were involved in the reactions with amines, imidazole, as well as with anions of these dimethylamino oximes. The glycidyl ether epoxide ring opening by amines under microwave irradiation conditions proceeds considerably faster than upon convection heating.

Synthesis and characterization of some novel 4-furyl substituted 3-imidazoline 3-oxides

Novel 4-furyl substituted 3-imidazoline 3-oxides were synthesized by the reaction of 2-bromo-1- (2-furanyl)ethanone oxime with aromatic amines and aldehydes, including formaldehyde, using one pot procedures involving the reactions of in situ formed α-amino oximes with aldehydes and also by one pot procedures involving the reactions of in situ formed imines with α-halo oximes.

Synthesis of α-amino oximes and bis-α-amino oximes from the monoterpene hydrocarbons 3-carene and α-pinene and α, ω-diamines

The reaction of nitroso chlorides of natural monoterpene hydrocarbons, 3-carene and α-pinene, with simple α,ω-diamines (1,2-diaminoethane, 1,3-diaminopropane, piperazine, 1,6-diaminohexane, diethylenetriamine) results in the formation of α-amino oximes and bis-α-amino oximes. The product structures were proved by spectroscopy. The procedures of separation and purification of diamino oximes and diamino dioximes are described. Detailed analysis of the 1H and 13C NMR spectra of the new chiral nitrogen-containing derivatives was carried out.

Unusual acid-induced heterocyclisation of caryophyllene-type α-amino oximes: X-ray structure of (1 S,2 S,5 R,8 S)-1,4,4,8-tetramethyl-8-morpholin-4-yl-11-oxa-10-azatricyclo[7.2.2.0 2,5]tridec-9-ene

The acid-catalysed cyclisation of caryophyllene-type α-amino oximes results in the formation of new bridged heterocycles with the 5,6-dihydro-4H-[1,2]oxazine moiety.

Sodium borohydride in an acetonitrile medium: An efficient reagent for reductive Beckmann type fragmentation of α-amino oximes

When treated with sodium borohydride in boiling acetonitrile, α-amino oximes are transformed to the corresponding ω-amino nitriles in 31–87% yield. Easily available α-amino oximes with cyclohexane, methylcyclohaxene, p-menthane, carane, pinane, and caryophyllane carbon skeletons are tested. The reaction was found to proceed only in an aliphatic nitrile medium; the specific role of a nitrile is discussed. Beckmann synchronous mechanism was confirmed for the fragmentation stage followed by reduction of the intermediate immonium salt.

Synthesis of monoterpenic α-amino ketones

Terpenic α-amino ketones have been prepared in good yield by treatment of the corresponding α-amino oximes with Ti(III) salts; all other known methods of deoximation give unacceptably low yields.

Reductive Beckmann's Type Fragmentation of α-Amino Oximes by Sodium Borohydride: A New Synthetic Pathway to ω-Amino Nitriles

Treatment of cyclic α-amino oximes with sodium borohydride in acetonitrile is a new convenient route to ω-amino nitriles.

Stereochemistry of α-Amino Oximes From the Monoterpene Hydrocarbons Car-3-ene, Limonene and α-Pinene

The conformation and configuration of the α-amino oximes derived from the terpene hydrocarbons car-3-ene, limonene and α- pinene have been determined by n.m.r. spectroscopy (high-field 1H n.m.r., 13C n.m.r., INADEQUATE technique), molecular mechanics calculations and X-ray crystallographic analysis. The crystal structure of (lS,3S,6R)-3-dimethylamino-caran-4-one (E)-oxime has been determined by X-ray diffraction; crystals are orthorhombic, space group P 212121 with a 11.421(2), b 13.223(2), c 16.992(4) �, Z 8. Refinement on 1730 observed reflections measured with Cu K α radiation converged at R 0.053.

Conversion of Terpenic Compounds to ω-Ketonitriles

Abstract Conversion of unsaturated terpenoids with trisubstituted oarbon-oarbon double bond into α-amino oximes followed by treatment with phosphorus pentaohloride results in the formation of aeco-terpenic ω-keto nitriales.

Synthesis of imidazole derivatives from ?-hydroxylamino oximes (review)

Data on the synthesis of imidazoline N-oxides from α-hydroxylamino oximes and α-amino oximes are collected in this review. The transformations of imidazoline N-oxides into N-oxides of imidazoles and 2H- and 4H-imidazoles and stable iminoxyl radicals and some properties of the compounds formed are examined.