New Type of Skipped Oligoaziridines: Synthesis of New Fatty AcidDerivatives Containing Aziridine Functions

Abstract

The first successful preparation of the aziridines methyl cis‐9,10;cis‐12,13‐diepiminooctadecanoate (3) derived from linoleic acid, and methyl cis‐9,10;cis‐12,13;cis‐15,16‐triepiminooctadecanoate (6) derived from linolenic acid, is reported. Remarkably, the bis‐ and trisaziridine were obtained in a reaction sequence that consists of only two steps, using technically pure methyl esters of epoxidized sunflower and linseed oil. The conversion of methyl 9,10;12,13‐diepoxyoctadecanoate (1), with sodium azide and ammonium chloride in ethanol in the presence of water, yielded the new diazidodihydroxy compound methyl 9(10),12(13)‐diazido‐10(9),13(12)‐dihydroxyoctadecanoate (2) in the first step. 2 was obtained as a regioisomeric mixture. The reaction of 2 with triphenylphosphane led to the bisaziridine 3. The analogous conversion of methyl 9,10;12,13;15,16‐triepoxyoctadecanoate (4), via the new triazidotrihydroxy compound methyl 9(10),12(13),15(16)‐triazido‐10(9),13(12),16(15)‐trihydroxyoctadecanoate (5), afforded trisaziridine 6.

In Coatings, Adhesives, and Laminates

“…Aziridines, characterized by the presence of two carbon atoms and one nitrogen atom in a three -membered ring, are the simplest heterocyclic systems and are extremely susceptible to cleavage due to ring strain [57] . Acidfunctional latexes crosslinked with aziridines have been employed as 2K, clear, interior wood coatings.…”

Aziridine alkaloids as potential therapeutic agents

“…Preparation of the fatty acid aziridines (106-115) has been described [148]. Bis(aziridine) Me cis-9,10;cis-12,13-diepimino-octadecanoate, derived from linoleic acid, and tris(aziridine) and Me cis-9,10;cis-12,13;cis-15,16-triepimino-octadecanoate, both derived from linolenic acid, showed cytotoxic and antimicrobial activity as well as remarkable antitumor-promoting and useful neuroprotective effects [149].…”