62366-56-7Relevant academic research and scientific papers
Enantioselective Alkynylation of 2-Trifluoroacetyl Imidazoles Catalyzed by Bis-Cyclometalated Rhodium(III) Complexes Containing Pinene-Derived Ligands
Zheng, Yu,Harms, Klaus,Zhang, Lilu,Meggers, Eric
supporting information, p. 11977 - 11981 (2016/08/16)
Chiral rhodium(III) complexes containing two cyclometalating 2-phenyl-5,6-(S,S)-pinenopyridine ligands and two additional acetonitriles are introduced as excellent catalysts for the highly enantioselective alkynylation of 2-trifluoroacetyl imidazoles. Whe
Synthesis, Stability, and Photoreactivity of Diazirinyl-Substituted N-Heterocycles Based on Indole, Benzimidazole, and Imidazole
Raimer, Bj?rn,Wartmann, Thomas,Jones, Peter G.,Lindel, Thomas
, p. 5509 - 5520 (2014/10/15)
The synthesis, thermal stability, and photoreactivity of trifluoromethyl diazirines installed at the heterocyclic section of N-methylindole, N-methylbenzimidazole, and at N-methylimidazole were investigated. N-Tosyl-3-diazirinylindole and N-methyl-2-diazirinylbenzimidazole proved to be thermally stable, whereas the corresponding 2-diazirinylindole was not. The least stable was 2-diazirinylimidazole, which underwent rapid decomposition. Quenching with ethanol indicated that the corresponding carbene was formed. Decomposition is rationalized by exothermic coarctate ring-opening of the carbene. Quantum mechanical calculations [B3LYP/6-311G(2d,2p)] predict singlet ground states of all carbenes. Accordingly, Friedel-Crafts alkylation products were formed on irradiation (350 nm, Rayonet) of the N-methylbenzimidazole-based diazirine in the presence of phenol.
2-(Trifluoroacetyl)imidazoles, 2-trifluoroacetyl-1,3-thiazoles, and 2-trifluoroacetyl-1,3-oxazoles
Khodakovskiy, Pavel V.,Volochnyuk, Dmitriy M.,Panov, Dmitriy M.,Pervak, Igor I.,Zarudnitskii, Evgenij V.,Shishkin, Oleg V.,Yurchenko, Aleksandr A.,Shivanyuk, Alexander,Tolmachev, Andrey A.
, p. 948 - 956 (2008/09/21)
A facile method of trifluoroacylation of imidazoles, 1,3-thiazoles, and 1,3-oxazoles with trifluoroacetic anhydride resulted in a set of heterocyclic trifluoromethyl-containing ketones. Unlike common ketones, these compounds form stable hydrates and enter into noncatalytic ene reactions with terminal olefins affording the corresponding allyl alcohols. Georg Thieme Verlag Stuttgart.
