Synthesis of sulfonate derivatives of 4-heteryl-isoxazoles

Palladium‐Catalyzed Intramolecular Cyclization of Nitroalkenes: Synthesis of Thienopyrroles

“…( E )‐2‐Methyl‐5‐(2‐nitropropenyl)thiophene (1g): Method A. Yellow solid; 72 % yield. 1 H NMR (300 MHz, CDCl 3 , 300 K): δ = 8.22 (s, 1 H, H alkenyl ), 7.26 (d, J = 3.3 Hz, 1 H, H thioph ), 6.86 (d, J = 3.6 Hz, 1 H, H thioph ), 2.58 (s, 3 H, CH 3 ), 2.52 ppm (s, 3 H, CH 3 ).…”

Primary nitro compounds: progress in the synthesis of isoxazoles by condensation with aldehydes or activated ketones

“…Nitrobutane reacts similarly (2, R = n-Pr). 28 The reaction between nitroethane and thiophene-2-carbaldehyde can be selected as an illustrative case (Scheme 4). The reaction yields isoxazole 8 (45%, R 1 = Me and R = 2-thienyl) by heating with an inorganic base (Cs 2 CO 3 ), 29 while it yields the Henry product 4 (65-95%, R 1 = Me and R = 2-thienyl) by heating with ammonium acetates (acetic acid and n-butylamine or other amines like cyclohexylamine or NH 3 ).…”

Novel 1-(1-Arylimiazolin-2-Yl)-3-Arylalkilurea Derivatives with Modulatory Activity on Opioid MOP Receptors

“…Other branched arylalkylamines were synthesized from the beginning. 1-Arylpropyl-2-amine derivatives (6a-r) were obtained from nitroethane and aromatic aldehydes via Henry's method (acetic acid, ammonium acetate, catalytic reduction with hydrogen in the presence of Raney nickel) [24,25] or heteroaromatic aldehydes (methanol in the presence of butyl amine, reduction with lithium aluminum tetrahydride) [26]. Benzylideneacetone derivatives were obtained via the Cleisen-Schmidt method [27].…”

“…Further on, they were transformed into oximes [28]. The reduction of oximes with hydrogen and Raney nickel or with lithium aluminum tetrahydride led to respective 1-arylbutyl-3-amines (7a-p) [26,29]. The presence of the urea moiety diminished the solubility of obtained compounds, whereas the introduction of longer and branched aliphatic linkers improved it.…”