CAS: 19485-38-2; 1-Methylimidazole-4,5-Dicarboxylic Acid

主要参考文献

参考标题:Convenient Synthesis Of Methyl 1-Methyl-2,4-Dibromo-5-Imidazolecarboxylate
作者:John F. O'Connell,Jonathan Parquette,William E. Yelle,Wilhelm Wang,Henry Rapoport
摘要: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 26% 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.

合成参考文献

摘要:Grimmett, M. R., Science of Synthesis, (2002) 12, 499.
摘要:Grimmett, M. R., Science of Synthesis, (2002) 12, 482.