Synthesis of 2, 3 fatty aziridines

Abstract

A new route for the synthesis of 2,3-aziridines is described. The reaction of methyl 2,3-dibromohexadecanoate (I1) with ammonia at 0 C gave methyl 2-bromohexadec-2-enoate (II1, ca. 93%). Compound III, on further treatment with ammonia at 25 C, gave methyl 2-aminohexadec-2-enoate (IV, ca. 5%), methyl trans-2,3-epiminohexadecanoate (V, ca. 64%), methyl cis-2,3-epiminohexadecanoate (VI, ca 24%) and trans-2,3-epirninohexadecamide (Vll, ca 3%). The structures were established with the help of elemental analyses and infrared (IR), nuclear magnetic resonance (NMR) and mass spectral analyses.

Enantioselective synthesis of aziridines using asymmetric transfer hydrogenation as a precursor for chiral derivatives used as bonding agent for rocket solid propellants

“…They have shown biological properties and are pivotal targets for the synthesis of chiral functionalized compounds. They are a rich source of important pharmaceuticals and adrenoceptor blocking agents 1 . Their derivatives have been studied as possible agents for the treatment of certain types of cancer.…”

Aziridination of Methyl Long-chain Alkenoates Using Chloramine-T

“…19 The aziridine derivatives of fatty acids have attracted great interest because of their significant biological properties and synthetic potential. 20 Numerous methods [19][20][21][22][23][24][25] have been developed to prepare the fatty aziridines but there is still a need for a new and easy method for their preparation. Keeping in mind the biological and synthetic potential of the aziridines we have tried to prepare the aziridine derivatives of internal and terminal olefinic fatty esters, which can further be used as intermediates for the synthesis of highly functionalised fatty compounds and can be tested for their biological activities.…”