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DOI: 10.1055/s-1995-4088
Improved Synthesis of Thromboxane A2 Receptor Antagonists with a Dibenzoxepin Ring System
Publication History
Publication Date:
31 December 2000 (online)
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Two derivatives of sodium (E)-11-[2-(1-benzimidazolyl)ethylidene]-11-oxo-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate, novel non-prostanoid 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.
(E)-selective - regioselective - 1-azadiene - dibenzoxepin - thromboxane A2 antagonist