ArticleChemistry (Weinheim an der Bergstrasse, Germany)2022
Anomeric Stereoauxiliary Cleavage of the C-N Bond of d-Glucosamine for the Preparation of Imidazo[1,5-a]pyridines.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 3 papers.
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3 citing papers in PubMed.
- Imidazopyridine Family: Versatile and Promising Heterocyclic Skeletons for Different Applications.Molecules (Basel, Switzerland) · 2024Review
- A recyclable stereoauxiliary aminocatalyzed strategy for one-pot synthesis of indolizine-2-carbaldehydes.Communications chemistry · 2023Article
- Anomeric Stereoauxiliary Cleavage of the C-N Bond of d-Glucosamine for the Preparation of Imidazo[1,5-a]pyridines.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
Corrections and comments
- Erratum issued
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8 authors.
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Abstract
The targeted cleavage of the C-N bonds of alkyl primary amines in sustainable compounds of biomass according to a metal-free pathway and the conjunction of nitrogen in the synthesis of imidazo[1,5-a]pyridines are still highly challenging. Despite tremendous progress in the synthesis of imidazo[1,5-a]pyridines over the past decade, many of them can still not be efficiently prepared. Herein, we report an anomeric stereoauxiliary approach for the synthesis of a wide range of imidazo[1,5-a]pyridines after cleaving the C-N bond of d-glucosamine (α-2° amine) from biobased resources. This new approach expands the scope of readily accessible imidazo[1,5-a]pyridines relative to existing state-of-the-art methods. A key strategic advantage of this approach is that the α-anomer of d-glucosamine enables C-N bond cleavage via a seven-membered ring transition state. By using this novel method, a series of imidazo[1,5-a]pyridine derivatives (>80 examples) was synthesized from pyridine ketones (including para-dipyridine ketone) and aldehydes (including para-dialdehyde). Imidazo[1,5-a]pyridine derivatives containing diverse important deuterated C(sp
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