Two derivatives of sodium (E)-11-[2-(1 1-oxo-6,11-dihydrodibenz[b,e]ox
epin-2-carboxylate, novel nonprostanoid thromboxane A(2) (TXA(2)) rece
ptor antagonists, were synthesized from methyl 1-oxo-6,11-dihydrodiben
z[b,e]oxepin-2-carboxylate. The carbonyl group at C11 was converted in
to a formylmethylene, then into a 1-azadiene moiety by reaction with a
2-aminoformanilide derivative. Stereo- and regioselective elaboration
of the unsymmetrical imidazoles was achieved through a sequence of th
e transformation of E,Z-1-azadiene intermediates to E isomers under ac
idic conditions followed by cyclization to imidazoles.