Several phosphorus-substituted
N-acylated cyanoaziridines
2 and
N-carbamoylated cyanoziridines
5 were prepared in good to high yields.
N-Acylated cyanoaziridines
2 were used, after ring expansion, in an efficient synthesis of oxazoline derivative
3a and in a completely regio-controlled reaction in the
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Several phosphorus-substituted
N-acylated cyanoaziridines
2 and
N-carbamoylated cyanoziridines
5 were prepared in good to high yields.
N-Acylated cyanoaziridines
2 were used, after ring expansion, in an efficient synthesis of oxazoline derivative
3a and in a completely regio-controlled reaction in the presence of NaI. Conversely,
N-carbamoyl cyanoaziridines
5 reacted with NaI to obtain a regioisomeric mixture of 2-aminocyanooxazolines
7. Mild acidic conditions can be used for the isomerization of
N-thiocarbamoyl cyanoaziridine
6a into a 2-aminocyanothiazoline derivative
8a by using BF
3·OEt
2 as a Lewis acid. Likewise, a one pot reaction of
NH-cyanoaziridines
1 with isocyanates obtained 2-iminocyanooxazolidines
9 regioselectively. This synthetic methodology involves the addition of isocyanates to starting cyanoaziridines to obtain
N-carbamoyl cyanoaziridines
5, which after the ring opening, reacts with a second equivalent of isocyanate to give the final 2-imino cyanooxazolidines
9. In addition, the cytotoxic effect on the cell lines derived from human lung adenocarcinoma (A549) was also screened. 2-Iminooxazolidines
9 exhibited moderate activity against the A549 cell line in vitro. Furthermore, a selectivity towards cancer cells (A549) over non-malignant cells (MCR-5) was detected.
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