19485-38-2Relevant articles and documents
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Efros et al.
, p. 455,456; engl. Ausg. S. 479, 480 (1956)
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Efficient synthesis of trisimidazole and glutaric acid bearing porphyrins: Ligands for active-site models of bacterial nitric oxide reductase
Collman, James P.,Yan, Yi-Long,Lei, Jianping,Dinolfo, Peter H.
, p. 923 - 926 (2007/10/03)
Ligands (1) for active-site models of bacterial nitric oxide reductase (NOR) have been efficiently synthesized. These compounds (1) feature three imidazolyl moieties and one carboxylic acid residue at the FeB site, which represent the closest available synthetic model ligands of NOR active center. The stereo conformations of these ligands are established on the basis of steric effects and 1H NMR chemical shifts under the ring current effect of the porphyrin.
Convenient Synthesis of Methyl 1-Methyl-2,4-dibromo-5-imidazolecarboxylate
O'Connell, John F.,Parquette, Jonathan,Yelle, William E.,Wang, Wilhelm,Rapoport, Henry
, p. 767 - 771 (2007/10/02)
Three syntheses of methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8) are presented.One proceeds from sarcosine via ring closure, bromination, and desulfurization.The second uses N-methylimidazole, polybromination, and selective halogen-metal interchange.The third and most efficient and preparatively useful route begins with diaminomaleonitrile (13).Ring closure with triethyl orthoformate followed by methylation and hydrolysis affords 1-methyl-4,5-imidazoledicarboxylic acid (16).Regioselective decarboxylation followed by esterification yields methyl 1-methyl-5-imidazolecarboxylate (18).Subsequent dibromination gives the completely substituted imidazole 8.The primary purification in this sequence is fractional sublimation of 18 after the esterification step.An overall yield of 26percent is achieved from diaminomaleonitrile (13) to methyl 1-methyl-2,4-dibromo-5-imidazolecarboxylate (8), which is a key intermediate for the synthesis of tricyclic imidazo cooked food mutagens.
