Tetrahedron

Rearrangements of tetrahydroimidazo [1, 5-b] isoxazole-2, 3-dicarboxylates to pyrrolo [1, 2-e] imidazol-6-ols, precursors of 2, 5-dihydro-1H-pyrrole derivatives

N Coşkun, M Çetin

文献索引：Coskun, Necdet; Cetin, Meliha Tetrahedron, 2009 , vol. 65, # 3 p. 648 - 658

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被引用次数: 6

摘要

Isoxazolines 2 from the cycloaddition of imidazoline 3-oxides 1 with DMAD rearrange in the presence of methoxide to give cis-3-methoxy-7-(methoxycarbonyl)-2, 7a-diaryl-5-oxo-2, 3, 5, 7a-tetrahydro-1H-pyrrolo [1, 2-e] imidazol-6-olates 3 with 100% de. The acidic hydrolysis of 3 led to kinetically controlled formation of methyl 1-formyl-4-hydroxy-5-oxo-2-phenyl-2- ((arylamino) methyl)-2, 5-dihydro-1H-pyrrole-3-carboxylates 6a–e. The intramolecular ...