Ring Opening of Epoxy Fatty Esters by Nucleophile to Form the Derivatives of Substituted &amp;lt;i&amp;gt;β&amp;lt;/i&amp;gt;-Amino Alcohol

Himani Varshney,Aiman Ahmad,Abdul Rauf

doi:10.4236/fns.2013.49a1004

Abstract

The nucleophilic ring opening of epoxy fatty esters was carried out using the amino-1,2,4-triazole to yield substituted derivatives of β-amino alcohol. The synthesis of the substituted beta amino alcohols has been achieved by refluxing equimolar quantities of long chain epoxy esters (epoxy fatty esters) and 4-amino-1,2,4-triazole in dichloromethane to yield following compounds, methyl 10-(4'-amino-1',2',4'-triazole)-11-hydroxy undecanoate (V), methyl 9-(4'-amino-1', 2',4'-triazole)-10-hydroxy octadecanoate (VI), methyl 9-(4'-amino-1',2',4'-triazole)-10,12-dihydroxy octadecanoate (VII), methyl 12-(4'-amino-1',2',4'-triazole)-9,13-dihydroxy octadecanoate (VIII). Epoxides of esters of fatty acids were obtained by reaction of esters of fatty acids with mchloroperbenzoic acid. All the newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR and mass spectrometry.

Highlights

Result and DiscussionVarious heterocyclic compounds from fatty esters bearing terminal or internal double bond were reported as potent dipolarophiles
Introduction βAmino alcohols are very important class of organic compound and this type of organic moiety is found in various biologically active alkaloids and peptides [1]
The synthesis of the substituted beta amino alcohols has been achieved by refluxing equimolar quantities of long chain epoxy esters and 4-amino-1,2,4-triazole in dichloromethane to yield following compounds, methyl 10-(4'-amino-1',2',4'-triazole)-11-hydroxy undecanoate (V), methyl 9-(4'-amino-1', 2',4'-triazole)-10-hydroxy octadecanoate (VI), methyl 9-(4'-amino-1',2',4'-triazole)-10,12-dihydroxy octadecanoate (VII), methyl 12-(4'-amino-1',2',4'-triazole)-9,13-dihydroxy octadecanoate (VIII)

Summary

Result and Discussion

Various heterocyclic compounds from fatty esters bearing terminal or internal double bond were reported as potent dipolarophiles. The ring opening reaction of terminal, I, and internal, II-IV, epoxy fatty esters with amino triazole resulted in the formation of inseparable mixtures, V-VIII, of β-amino alcohol in appreciable yield (68% to 74%). Similar situation was observed in the case of terminal epoxy ester, I, there was a choice for the nucleophile to attack from the less hindered side product V was formed as a major product. Another isomer may be formed in trace amount, but could not be isolated.

Experimental

H C R2 OH

Conclusion