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. 2020 Nov 26:16:2903-2910.
doi: 10.3762/bjoc.16.239. eCollection 2020.

Synthesis of imidazo[1,5- a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

Dmitrii A Aksenov  1 , Nikolai A Arutiunov  1 , Vladimir V Maliuga  1 , Alexander V Aksenov  1 , Michael Rubin  1   2
Affiliations

Synthesis of imidazo[1,5- a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

Dmitrii A Aksenov et al. Beilstein J Org Chem. .

Abstract

Imidazo[1,5-a]pyridines were efficiently prepared via the cyclization of 2-picolylamines with nitroalkanes electrophilically activated in the presence of phosphorous acid in polyphosphoric acid (PPA) medium.

Keywords: cyclization; heterocycles; imidazo[1,5-a]pyridines; nitroalkanes; polyphosphoric acid.

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Figures

Figure 1
Figure 1
Biologically active imidazo[1,5-a]pyridines.
Scheme 1
Scheme 1
Activation of nitroalkanes towards nucleophilic attack by amines.
Scheme 2
Scheme 2
Mechanistic rationale.
Scheme 3
Scheme 3
Reaction of the N-tosylate 17 with electrophilic nitroalkanes.
Scheme 4
Scheme 4
Reaction of 2-(aminomethyl)pyridine (12) with electrophilic nitroalkanes.
Scheme 5
Scheme 5
Reaction of the 2-(aminomethyl)quinolines 18 with electrophilic nitroalkanes.
Scheme 6
Scheme 6
Reactivity of α-nitroacetophenone (1h) and α-nitroacetic ester (1i).
See this image and copyright information in PMC

References

    1. Calcul L, Longeon A, Al Mourabit A, Guyot M, Bourguet-Kondracki M-L. Tetrahedron. 2003;59:6539–6544. doi: 10.1016/s0040-4020(03)01069-x. - DOI
    1. Pettit G R, Collins J C, Knight J C, Herald D L, Nieman R A, Williams M D, Pettit R K. J Nat Prod. 2003;66:544–547. doi: 10.1021/np020012t. - DOI - PubMed
    1. Yu H-B, Yang F, Sun F, Ma G-Y, Gan J-H, Hu W-Z, Han B-N, Jiao W-H, Lin H-W. J Nat Prod. 2014;77:2124–2129. doi: 10.1021/np500583z. - DOI - PubMed
    1. Augustin E, Pawłowska M, Polewska J, Potega A, Mazerska Z. Cell Biol Int. 2013;37(2):109–120. doi: 10.1002/cbin.10018. - DOI - PubMed
    1. Isambert N, Campone M, Bourbouloux E, Drouin M, Major A, Yin W, Loadman P, Capizzi R, Grieshaber C, Fumoleau P. Eur J Cancer. 2010;46:729–734. doi: 10.1016/j.ejca.2009.12.005. - DOI - PubMed

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