91533-85-6Relevant academic research and scientific papers
One-step synthesis of N, N′-substituted 4-imidazolidinones by an isocyanide-based pseudo-five-multicomponent reaction
Attorresi, Cecilia I.,Bonifazi, Evelyn L.,Ramírez, Javier A.,Gola, Gabriel F.
supporting information, p. 8944 - 8949 (2018/12/10)
A pseudo-five-multicomponent reaction involving an isocyanide, a primary amine, two molecules of formaldehyde and water is reported, which gives N,N′-substituted 4-imidazolidinones when trifluoroethanol is used as the solvent. The reaction proceeds with good yields and with a wide variety of amines and isocyanides, providing an efficient new entry to these heterocycles. A preliminary study of the reaction mechanism suggests that trifluoroethanol, although acting as the solvent, is directly involved as a reagent in the reaction pathway.
Mild Access to N-Formylation of Primary Amines using Ethers as C1 Synthons under Metal-Free Conditions
Mutra, Mohana Reddy,Dhandabani, Ganesh Kumar,Wang, Jeh-Jeng
supporting information, p. 3960 - 3968 (2018/09/10)
A new synthetic protocol has been developed for the synthesis of N-formamide derivatives using ethers as a C1 synthon under metal-free reaction conditions. The reaction is proposed to proceed through C?H functionalization, C?O cleavage, and C?N bond formation. This protocol is applicable to a variety of primary amines resulting in N-formamides in moderate to good yields. 1,4-dioxane was chosen as best C1 synthon after screening with various ethers. Mechanistic studies disclosed that the reaction proceeds through a radical pathway. While using α-amino ketones a α-alkylation product was formed rather than formylation. By replacing dioxane with Tetramethylethylenediamine (TMEDA) under standard conditions also gave the N-formamide derivatives in moderate yields. (Figure presented.).
Regiochemistry of nucleophilic substitution of pentachloropyridine with N and O bidentate nucleophiles
Poorfreidoni, Alireza,Ranjbar-Karimi, Reza,Kia, Reza
, p. 4398 - 4406 (2015/06/16)
Site reactivity of some enol-imines derived from N-aryl formamides with pentachloropyridine under basic conditions in dry CH3CN was investigated. The aromatic nucleophilic substitution of pentachloropyridine with enol-imines occurs at the 4-position of pyridine ring by both oxygen and nitrogen site of enol-imines. Nucleophilic attack by the oxygen of enol-imine gave corresponding oximino compounds as a mixture of E- and Z-isomers. In contrast, nucleophilic attack by the nitrogen of enol-imine gave the unexpected N,N-di-substituted aryl compounds. The structures of all the compounds were confirmed by IR, 1H NMR, 13C NMR and 19F NMR spectroscopy as well as elemental analysis and X-ray crystallography.
Survey reactivity of some N-aryl formamides with pentafluoropyridine
Ranjbar-Karimi, Reza,Poorfreidoni, Alireza,Masoodi, Hamid Reza
, p. 222 - 226 (2015/11/03)
Chemo selectivity of some N-aryl formamides with pentafluoropyridine under basic conditions in dry THF was investigated. The aromatic nucleophilic substitution of pentafluoropyridine with enol-imines derived from N-aryl formamides occurs at the 4-position of pyridine ring by both oxygen and nitrogen site of enol-imines depending on the nature of the aromatic ring substituent; with electron releasing group, nucleophilic attack was accomplished by oxygen atom and with an electron withdrawing group, the reaction of N-aryl formamide anions with pentafluoropyridine proceeded via nitrogen site.
A metal-free approach for transamidation of amides with amines in aqueous media
Srinivas, Mahesuni,Hudwekar, Abhinandan D.,Venkateswarlu, Vunnam,Reddy, G. Lakshma,Kumar, K. A. Aravinda,Vishwakarma, Ram A.,Sawant, Sanghapal D.
supporting information, p. 4775 - 4779 (2015/07/20)
An efficient, environmentally benign and a mild protocol for transamidation of amides with a variety of amines in the presence of K2S2O8 using stoichiometric quantity in aqueous conditions has been established. This method works under conventional thermal conditions and in microwave irradiation as well. A series of amides have been prepared using this reaction and this is a greener protocol for transamidation, which offers a diverse kind of substrate scope with exclusive product formation (yields 90-98%).
ZnO as a new catalyst for N-formylation of amines under solvent-free conditions
Hosseini-Sarvari, Mona,Sharghi, Hashem
, p. 6652 - 6654 (2007/10/03)
The treatment of amines with formic acid in the presence of ZnO under solvent-free conditions brings about highly and efficient N-formylation to give the corresponding formamides in excellent yields. The N-formylation reaction not only involves mild conditions, simple operation, and high yields but also high chemoselectivity.
Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents
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Page column 158, (2010/02/05)
This invention relates to 2-arylimino heterocycles, including 2-arylimino-1,3-thiazolidines, 2-arylimino-2,3,4,5-tetrahydro-1,3-thiazines, 2-arylimino-1,3-thiazolidin-4-ones, 2-arylimino-1,3-thiazolidin-5-ones, and 2-arylimino-1,3-oxazolidines, and their use in modulating progesterone receptor mediated processes, and pharmaceutical compositions for use in such therapies.
