Synthesis of fused imidazo[1,2-a]pyridines derivatives through cascade C(sp)-H functionalizations.

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ID: 58189
2019
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Abstract
An efficient and convenient synthesis of diversely substituted naphtho[1',2':4,5]imidazo[1,2-a]-pyridine derivatives from the cascade reactions of 2-arylimidazo[1,2-a]pyridines with a-diazo carbonyl compounds via Rh(iii)-catalyzed regioselective C(sp2)-H alkylation followed by intramolecular annulation is presented. Interestingly, when simple 2-arylimidazo[1,2-a]pyridines were used as the substrates, 5,6-disubstituted naphtho[1',2':4,5]imidazo[1,2-a]pyridines were efficiently obtained, whereas using 2-arylimidazo[1,2-a]pyridine-3-carbaldehydes as the substrates afforded naphtho[1',2':4,5]imidazo[1,2-a]-pyridine-5-carboxylates as the dominating products. Compared with literature methods for the synthesis of naphtho[1',2':4,5]imidazo[1,2-a]pyridine derivatives, the protocol presented herein has advantages such as easily obtainable substrates, simple operational procedure, high efficiency and excellent regio- and chemoselectivity.
Reference Key
li2019synthesisorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Li, Bin;Shen, Nana;Zhang, Xinying;Fan, Xuesen;
Journal Organic & biomolecular chemistry
Year 2019
DOI
10.1039/c9ob01744e
URL
Keywords
crystal structure ncn pincer organonickel phosphinimine

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