35342-94-0Relevant academic research and scientific papers
Iridium-Catalyzed Direct Amidation of Imidazoles at the C-2 Position with Isocyanates in the Presence of Hydrosilanes Leading to Imidazole-2-Carboxamides
Fukumoto, Yoshiya,Shiratani, Motohiro,Noguchi, Hikaru,Chatani, Naoto
supporting information, p. 3011 - 3018 (2021/03/03)
Regioselective coupling reaction of N -substituted imidazoles with isocyanates in the presence of a stoichiometric amount of hydrosilanes catalyzed by Ir 4(CO) 12to give imidazole-2-carboxamides is reported. Imidazoles bearing an (O -silyl)carboximidate group at the 2-position appear to be initially formed in the reaction; these are then hydrolyzed to the final products in situ. The addition of the hydrosilane was essential for the catalytic reaction to proceed. Substituents on the imidazole ring had no effect on the reaction, except for certain bulky substituents such as tBu and Ph groups at the 4-position. Triazoles such as 4-methyl-4 H -1,2,4-triazole and 1-methyl-1 H -1,2,4-triazole were also applicable to this C-H amidation, and the latter reaction proceeded regioselectively at the carbon atom between the sp 3and sp 2nitrogen atoms of the ring, and not between the two sp 2nitrogen atoms.
Phenylcarbamoylation of N-acetyl-1,2,4-triazolium-4-aminides revisited
Moderhack, Dietrich,Noreiks, Matthias
, p. 2113 - 2122 (2008/01/27)
The reaction of N-acetyl-1,2,4-triazolium-4-aminides (I, i.e. 1Aa-d) with phenyl isocyanate affords ring functionalized products (4a-d) rather than linear adducts (II). Analogous compounds are obtained from the triazolium-1-aminide (1Ae) and the imidazoli
α-nitrogen activating effect in the room temperature copper-promoted N-arylation of heteroarylcarboxamides with phenyl siloxane or p-toluylboronic acid
Lam, Patrick Y.S.,Deudon, Sophie,Hauptman, Elisabeth,Clark, Charles G.
, p. 2427 - 2429 (2007/10/03)
Heteroarylcarboxamides containing α-nitrogens undergo copper-promoted N-phenylation with hypervalent phenyl trimethylsiloxane at room temperature, in the absence of base and in air. Arylboronic acid can substitute for phenyl trimethylsiloxane as the organ
Di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine revisited. Their reactions with amines and alcohols
Basel, Yochai,Hassner, Alfred
, p. 6368 - 6380 (2007/10/03)
The reaction of BOC2O in the presence and absence of DMAP was examined with some amines, alcohols, diols, amino alcohols, and aminothiols. Often, unusual products were observed depending on the ratio of reagents, reaction time, polarity of solvent, pK(a) of alcohols, or type of amine (primary or secondary). In reactions of aliphatic alcohols with BOC2O/DMAP, we isolated for the first time carbonic-carbonic anhydride intermediates; this helps explain the formation of symmetrical carbonates in addition to the O-BOC products. In the case of secondary amines, we succeeded to isolate unstable carbamic-carbonic anhydride intermediates that in the presence of DMAP led to the final N-BOC product. The effect of N-methylimidazole in place of DMAP was also examined.
