Abstract
An iodine-mediated decarboxylative cyclization was developed from α-amino acids and 2-methyl quinolines under metal-free conditions, affording a variety of imidazo[1,5-a]quinolines with moderate to good yields.
Highlights
The imidazo[1,5-a]quinoline moiety is an important class of fused N-heterocyclic compounds such as skeletons of NK1 receptor ligands,[1] antitumor drug C-1311,2 potential antimicrobial natural product cribrostatin 6,3 inhibitor targeting phosphodiesterase 10A4 and highly efficient ligands of central benzodiazepine receptors.[5]
As the structure for the precursors of N-heterocyclic carbene[6] and other transformations,[7] much effort has been done for the synthesis of imidazo[1,5-a]quinolines
Zeng and Xu groups independently reported copper-catalyzed imidazole synthesis via the oxidative C–H amination reactions (Scheme 1a and b).[10]. These elegant protocols led to new reactivity pathways and made great progress in imidazole synthesis
Summary
The imidazo[1,5-a]quinoline moiety is an important class of fused N-heterocyclic compounds such as skeletons of NK1 receptor ligands,[1] antitumor drug C-1311,2 potential antimicrobial natural product cribrostatin 6,3 inhibitor targeting phosphodiesterase 10A4 and highly efficient ligands of central benzodiazepine receptors.[5]. Zeng and Xu groups independently reported copper-catalyzed imidazole synthesis via the oxidative C–H amination reactions (Scheme 1a and b).[10]. These elegant protocols led to new reactivity pathways and made great progress in imidazole synthesis. These reported methods still suffered from the usage of transitionmetal catalysts. Our group developed previously some oxidative C–H amination reactions for imidazole synthesis under metal-free conditions.[11]. The main drawbacks are the narrow scope of the substrates and the difficulty of the available starting materials. A more environmental-friendly methodology with readily available starting materials for the preparation of imidazo[1,5-a]quinolines is highly desirable
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