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

@article{LieKenJie2001CyclodehydrationRO,
  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},
  journal={Lipids},
  year={2001},
  volume={36},
  pages={201-205}
}
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

TLDR
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

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