1.
Chemistry
; 25(6): 1456-1460, 2019 Jan 28.
Artigo
em Inglês
| MEDLINE
| ID: mdl-30489663
RESUMO
Synthesis and isolation of highly unstable azirinobenzoxazole and benzoxazines in a chemodivergent fashion from aryl azido vinylogous carbonates by simple change in transition metal acetate is described. Thermal or rhodium(II) acetate-mediated decomposition of these azides gave dihydroazirino benzoxazole. Their nickel(II) acetate-promoted reaction gave 4-dihydro-2H-benzoxazines, whereas copper(II) acetate led to the corresponding oxidized imine derivatives. Benzaoxazine derivative could be kinetically resolved using a proline-catalyzed Mannich reaction. The benzoxazines were rapidly elaborated to angularly fused tetracyclic systems and coumarin-fused derivatives in a "one pot" fashion.