The oxidative rearrangement of furan-2-carboximidamides: preparation and properties of 2-acylaminofurans

Discovery and Biological Evaluation of 5-Aryl-2-furfuramides, Potent and Selective Blockers of the Nav1.8 Sodium Channel with Efficacy in Models of Neuropathic and Inflammatory Pain

“…5-(4-Chlorophenyl)- N -[3-(4,5-dihydrooxazol-2-yl)phenyl]furan-2-carboxamide Hydrochloride (25). 25 was prepared from 21 and [3-(4,5-dihydro-oxazol-2-yl)phenyl]amine . The product was converted to the HCl salt by treatment of the ethanolic solution with HCl in ether: mp 225–227 °C (dec); 1 H NMR (400 MHz, DMSO- d 6 ) δ 10.34 (s, 1H), 8.81 (t, J = 1.7 Hz, 1H), 8.02 (d, J = 8.8 Hz, 2H), 8.00–7.97 (m, 1H), 7.62 (dt, J = 8.1, 1.2 Hz, 1H), 7.58 (d, J = 8.8 Hz, 2H), 7.47 (t, J = 8.0 Hz, 1H), 7.44 (d, J = 3.4 Hz, 1H), 7.24 (d, J = 3.7 Hz, 1H), 4.43 (t, J = 9.7 Hz, 2H), 3.98 (t, J = 9.5 Hz, 2H); MS (DCI/NH 3 ) m / z 367 (M + H) + .…”

“…30 The preparation of several isosteric replacements for the carbonyl residue in 3 is outlined in Scheme 3. Addition of 3-aminotoluene to 2-cyanofuran 17 31 in the presence of trimethylaluminum provided amidine 18, which could be conveniently isolated as the hydrochloride salt. Exposure of 3 to Lawesson's reagent 32 generated 19, which was further elaborated to the corresponding cyanoamidine 20 by S-methylation and reaction with cyanamide.…”

Low catalyst loading ligand-free palladium-catalyzed direct arylation of furans: an economically and environmentally attractive access to 5-arylfurans

“…This journal is © The Royal Society of Chemistry 2009 22 4-Bromonitrobenzene (0.202 g, 1 mmol), 2-cyanofuran (0.186 g, 2 mmol), AcOK (0.196 d 154.3, 134.8, 133.6, 131.3, 129.8, 127.4, 126.6, 124.4, 118.6, 111.7, 111.5, 106.6. Elemental analysis: calcd (%) for C 12 H 6 N 2 O (194.19): C 74.22, H 3.11; found: C 74.10, H 3.04.…”

Acyclic and Cyclic Ureas (Update 2013)

“…[ Synthesis of N-(Iminomethyl)ureas N-(Iminomethyl)ureas or formamidine ureas of the general structure shown in Scheme 115 can be prepared by using a standard method for urea synthesis, namely the reaction between an amino group, in this case one located in an amidine, and an isocyanate. [301] Scheme 115 General Structure of N-(Iminomethyl)ureas…”