Grimmett M. Ross. Imidazole and Benzimidazole Synthesis

Academic Press, 1997. – 265 p. (Best Synthetic Methods — sub-series Key Systems and Functional Groups)This is the second book in the sub-series of Best Synthetic Methods — Key Systems and Functional Groups and is particularly close to my heart. As a young research chemist I recall we formulated the 'Benzimidazole Rule'. This stated that given the right number of carbons and nitrogens, any starting material would ultimately end up as a benzimidazole!
The imidazole and benzimidazole ring systems are, of course, not just interesting and a source of endless research pleasure but are key systems both in nature (such as the amino acid histidine, vitamin B12, a component of DNA base structure and purines, histamine, biotin, etc.) and thus obviously in pharmaceutical, veterinary and agrochemical products such as cimetidine (tagamet), azomycin, metronidazole, misonidazole, chlotrimazole, thiabendazole, benomyl to name but a few. To underline this ubiquity of their medicinal applications, over one third of the pages of the excellent compilation of the Drug Compendium in Volume 6 of Comprehensive Medicinal Chem-istry (Pergamon Press, 1990) contain imidazole or benzimidazole units. Other important uses of these systems include high temperature polymer products and dyestuffs.
Ross Grimmett is an established master in the field, having compiled several authoritative reviews of these systems. He has now lent his effort to doing synthetic chemists a great favor with this wide-ranging 'cookery book' where every type of synthetic problem, both of ring synthesis and of incorporation of key functionality have been addressed and lavishly exemplified with actual preparations. I hope you will enjoy it as much as I have.Ring Synthesis by Formation of One Bond
Ring Syntheses Involving Formation of Two Bonds: [4 + 1] Fragments
Ring Syntheses Involving Formation of Two Bonds: [3 + 2] Fragments
Ring Syntheses which Involve Formation of Three or Four Bonds
Syntheses From Other Heterocycles
Aromatic Substitution Approaches to Synthesis
Synthesis of Specifically Substituted Imidazoles and Benzimidazoles Index of Compounds and Methods