Abstract
Contrary to reports in the early literature, 5-aminoimidazoles can be prepared in good yield as crystalline compounds. A study of their chemistry has shown that they behave as either C- or N-nucleophiles depending upon the nature of the electrophile. These addition and addition-elimination reactions provide useful new routes to nitrogen heterocycles. An important naturally occurring 5-aminoimidazole, aminoimidazole ribonucleotide (AIR) is a biosynthetic precursor of purines and thiamine. The chemistry of 5-aminoimidazoles is discussed and a synthesis of the aminotmidazole ribonucleoside (AIRS) and its biomimetic transformation to novel purine analogues is presented.
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Department of Chemistry, Keele University, Keele, Staffordshire, ST5 5BG, England. Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1323–1331, October, 1995. Original article submitted July 15, 1995.
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Ramsden, C.A. 5-Aminoimidazole chemistry. Chem Heterocycl Compd 31, 1155–1162 (1995). https://doi.org/10.1007/BF01185582
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DOI: https://doi.org/10.1007/BF01185582