Synthesis p. 1257 - 1262 (1995)
Update date:2022-08-05
Topics:
Sugaya
Kato
Sakaguchi
Tomioka
Two derivatives of sodium (E)-11-[2-(1-benzimidazolyl)ethylidene]11-oxo-6,11-dihydrodibenz[b,e]o xepin-2-carboxylate, novel nonprostanoid thromboxane A2 (TXA2) receptor antagonists, were synthesized from methyl 11-oxo-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate. The carbonyl group at C11 was converted into 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 the transformation of E,Z-1-azadiene intermediates to E isomers under acidic conditions followed by cyclization to imidazoles.
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