Anomeric Stereoauxiliary Cleavage of the C-N Bond of
An anomeric stereoauxiliary approach for the synthesis of a wide range of imidazo[1,5-a]pyridines I (R1 = Me, 2-methylphenyl, pyridin-2-yl, etc.; R2 = 4-methoxyphenyl, naphthalen-1-yl, thiophen-2-yl, etc.) after cleaving the C-N bond of D-glucosamine (α-2° amine) from biobased resources was reported . This new approach expands the scope of readily accessible imidazo[1,5-a]pyridines I 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 2-acylpyridines (including para-dipyridine ketone) and aldehydes (including para-dialdehyde) R2CHO. Imidazo[1,5-a]pyridine I derivatives containing diverse important deuterated C(sp2)-H and C(sp3)-H bonds were also efficiently achieved. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1SDS of cas: 91-02-1).
Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.SDS of cas: 91-02-1