4785-79-9Relevant academic research and scientific papers
Photocatalytic Intramolecular C-H Amination Using N-Oxyureas as Nitrene Precursors
Ivanovich, Ryan A.,Polat, Dilan E.,Beauchemin, André M.
supporting information, p. 6360 - 6364 (2020/09/02)
Nitrenes are remarkable high-energy chemical species that enable direct C-N bond formation, typically via controlled reactions of metal-stabilized nitrenes. Here, in contrast, the combined use of photocatalysis with careful engineering of the precursor enabled C-H amination forming imidazolidinones and related nitrogen heterocycles from readily accessible hydroxylamine precursors. Preliminary mechanistic results are consistent with the formation of free carbamoyl triplet nitrenes as reactive intermediates.
First synthesis of the N(1)-bulky substituted imidazole 3-oxides and their complexation with hexafluoroacetone hydrate
Mloston, Grzegorz,Jasinski, Marcin
, p. 162 - 175 (2011/06/19)
Synthesis of new 2-unsubstituted imidazole 3-oxides bearing bulky substituents at the N(1) atom, based on the condensation of appropriate alkylamines, formaldehyde, and corresponding a-(hydroxyimino)ketone, is described. Treatment of imidazole 3-oxides with hexafluoroacetone hydrate (HFAH) yields crystalline 1:1 complexes in nearly quantitative yields. Heating of isolated complexes possessing phenyl ring at the C(4) atom of imidazole ring, results in their isomerization into imidazol-2-ones in fair yields. The formation of analogous complexes of HFAH with other azole N-oxides is also described. ARKAT-USA, Inc.
Reactions of 2-unsubstituted 1H-imidazole 3-oxides with 2,2-bis(trifluoromethyl)ethene-1,1-dicarbonitrile: A stepwise 1,3-dipolar cycloaddition
Mloston, Grzegorz,Jasinski, Marcin,Linden, Anthony,Heimgartner, Heinz
, p. 1304 - 1316 (2007/10/03)
The reaction of 1,4,5-trisubstituted 1H-imidazole-3-oxides 1 with 2,2-bis(trifluoromethyl)ethene-1,1-dicarbonitrile (7, BTF) yielded the corresponding 1,3-dihydro-2H-imidazol-2-ones 10 and 2-(1,3-dihydro-2H-imidazol- 2-vlidene)malononitriles 11, respectiv
Synthesis of imidazole derivatives using 2-unsubstituted 1H-imidazole 3- oxides
Mloston, Grzegorz,Celeda, Malgorzata,Prakash, G. K. Surya,Olah, George A.,Heimgartner, Heinz
, p. 728 - 138 (2007/10/03)
The reaction of 1,4,5-trisubstituted 1H-imidazole 3-oxides 1 with Ac2O in CH2Cl2 at 0-5°leads to the corresponding 1,3-dihydro-2H-imidazol-2-ones 4 in good yields. In refluxing Ac2O, the N-oxides 1 are transformed to N- acetylated 1,3-dihydro-2H-imidazol-2-ones 5. The proposed mechanisms for these reactions are analogous to those for N-oxides of 6-membered heterocycles (Scheme2). A smooth synthesis of 1H-imidazole-2-carbonitriles 2 starting with 1 is achieved by treatment with trimethylsilanecarbonitrile (Me3SiCN) in CH2Cl2 at 0-5°(Scheme 3).
