Carbene reactivity of 4-diazo-4H-imidazoles toward nucleophiles and aromatic compounds

The Journal of Organic Chemistry
Matthew R SmithChristopher J Moody

Abstract

Carbenes derived from diazoimidazolecarboxylates 4 under thermal or photochemical conditions undergo O-H and N-H insertion reactions with alcohols and amines, respectively, in moderate yield, in competition with reduction in good H-donor solvents. Dichloromethane reacts to give the corresponding 4-chloroimidazole. Aromatic hydrocarbons are excellent traps for the imidazolylidene carbene and lead to a range of arylimidazole derivatives 7. Reaction with pyridine leads to the first example of a pyridinium ylide 8 formed from an imidazolylidene carbene, whereas irradiation in hexafluorobenzene gives the imidazoazocine 11, presumably by way of an initial norcaradiene intermediate.

References

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Sep 1, 2004·European Journal of Medicinal Chemistry·Preeti GuptaRahul Jain
Jul 11, 2006·Journal of Combinatorial Chemistry·Chai Hoon SohYulin Lam

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Citations

Jun 27, 2017·Organic & Biomolecular Chemistry·Changcheng WangHua Cao
Aug 11, 2015·Organic & Biomolecular Chemistry·Zhaowen DongMitsuo Kira
Dec 14, 2018·Organic & Biomolecular Chemistry·Łukasz W CiszewskiDorota Gryko
Jan 22, 2011·The Journal of Organic Chemistry·Tryfon Zarganes-TzitzikasConstantinos A Tsoleridis

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