Cyclodehydration reactions of methyl 9,10-; 10,12-; and 9,12-dioxostearates with 1,2-diaminoethane under ultrasonic irradiation

  title={Cyclodehydration reactions of methyl 9,10-; 10,12-; and 9,12-dioxostearates with 1,2-diaminoethane under ultrasonic irradiation},
  author={Marcel S. F. Lie Ken Jie and Maureen M. L. Lau and Prabhavathi Kalluri},
Reaction of methyl 9,10-dioxostearate (1) and 9,12-dioxostearate (2) with 1,2-diaminoethane under concomitant ultrasonic irradiation (10–15 min, 60°C) in water furnished the corresponding 2,3-dihydropyrazine (4, 79%) and 1,2,3,4-tetrahydro-1,4-diazocine (5, 70%) derivatives, respectively. Reaction of methyl 10,12-dioxostearate (3) with 1,2-diaminoethane was successful only when glacial acetic acid was used instead of water under ultrasonic irradiation (4×10 min, 70°C) to give a 2,3-dihydro-1H-1… 

Fullerenoid lipids: First synthesis of structured triacylglycerols containing an aza-[60]fullerence unit

The nitrogen atom attached to the carbon cage formed a “[5,6]-open” type aza substructure, which was confirmed by the appearance of 31–32 signals in the region of δC 133–148 (carbon shifts of sp2 carbons of the cage in the 13C nuclear magnetic resonance spectra).

Synthesis and characterization of long-chain 1,2-dioxo compounds.

  • G. Knothe
  • Chemistry
    Chemistry and physics of lipids
  • 2002



Diazepines. Part V. 2,3-Dihydro-1H-1,4-diazepines

When equimolar mixtures of β-diketones and aliphatic 1,2-diamines are heated in acetic acid 2,3-dihydro-1H-1,4-diazepine derivatives are formed. If, however, 2 : 1 mixtures of these reactants are

Diazepines. Part VI. Condensation products from benzoylacetone and ethylenediamine

Under the appropriate conditions the reaction between benzoylacetone and ethylenediamine may give rise to 2,3-dihydro-5-methyl-7-phenyldiazepine (or a salt),

Synthesis of novel piperideine- and pyridine-containing long-chain fatty ester derivatives from methyl iso-ricinoleate

Oxidative rearrangement of methyl 9-azido-12,13-epoxy-stearate 2 with MeI, NaI and DMF and short-time concomitant ultrasonication at 120 °C yields exclusively 1,4- and 1,5-azido-oxo isomers 3 and 4,

Diazepines. Part XVI. Nuclear magnetic resonance spectra of 2,3-di-hydro-1H-1,4-diazepinium salts

The n.m.r. spectra of a number of 2,3-dihydro-1H-1,4-diazepinium perchlorates are discussed. They indicate that the dihydrodizepinium cation has a half-chair shape which inverts rapidly at room

Spectral properties and ring conformation of some novel 2,3-dihydro-1H-1,4-diazepinium cations

A series of 2,3-dihydro-1H-1,4-diazepinium salts, which includes fused ring systems of known ring-junction configuration, has been prepared. A study of the spectral properties indicates that this

Geometric and electronic structure of dicyanofuroxan by experiment and theory

Dicyanofuroxan (3,4-dicyano-1,2,5-oxadiazole 2-oxide), the precursor to the novel NCCNO species, has been studied in the solid and gas phases to obtain both structural and electronic information. The

Synthesis of pyridazine fatty ester derivatives in water: a sonochemical approach

Reactions induced by ultrasonic irradiation of methyl 9,12-dioxostearate with hydrazines in water in the presence of acidic alumina at 0–5 °C provide high yields of pyridazine fatty esters directly.

Synthetic Organic Sonochemistry

1. Theoretical Bases T. Lepoint, F. Lepoint-Mullie. 2. Sonochemistry of Solutions C. Petrier, J.-L. Luche. 3. Cycloadditions H. Fillion, J.-L. Luche. 4. Sonochemistry in Biphasic Systems A. Loupy,