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■ Imidazoquinolines as Diverse and Interesting Building Blocks: Review of Synthetic Methodologies

Zeinab Mahmoud and Mohsen Daneshtalab*

*School of Pharmacy, Memorial University of Newfoundland, St. John’s, NL, A1B 3V6, Canada

Abstract

Imidazoquinolines are interesting heterocyclic systems that depending on the position of fusion and the type of substituents display diverse biological and pharmaceutical properties. From the chemistry point of view, imidazoquinolines are heterocylic scaffolds resulting from the fusion between the 5-membered ring imidazole and the benzopyridine ring, quinoline. At least eight different combinations can be identified for these significant scaffolds. From the retrosynthetic point of view, imidazoquinolines can be prepared using one of two general approaches: imidazole-ring formation or pyridine-ring one. According to the type of imidazoquinoline and the position of the substituents either one of these two plans can be adopted. Pertinent to the specific plan to be used, different starting materials can be implanted as well. The most general starting materials are the diaminoquinolines and the aminobenzimidazoles. The main objective of this review article is to shed light on the reported synthetic pathways for each imidazoquinoline system.