Chiral oxazoline ligands containing a 1,2,4-triazine ring and their application in the Cu-catalyzed asymmetric Henry reaction

A novel synthesis of substituted 3‐amino and 3‐thio pyrimido[5,4‐e]‐1,2,4‐triazine‐5,7(1H,6H)‐diones

“…Application of these conditions to 3‐aminopyridine led to a complex reaction mixture without evidence of formation of 9g . However, under Buchwald‐Hartwig conditions (palladium[II] acetate, xantophos) [ 11 ] successful conversion to 9g occurred in 78% yield. Adducts 9a and 9d were Boc‐deprotected to 9b and 9e , respectively, under neutral conditions (trimethylsilyl triflate, 2,6‐lutidine) in 75%–87% yield.…”

“…Following a previously described procedure, [ 11 ] a mixture of anhydrous p ‐dioxane (2 ml), xantphos (20.44 mg, 0.035 mmol), and palladium(II) acetate (3.97 mg, 0.018 mmol) was charged into flask #1 to generate the catalyst, and a mixture of 8 (60 mg, 0.177 mmol), 3‐aminopyridine (16.62 mg, 0.177 mmol), potassium carbonate (488 mg, 3.53 mmol), and p ‐dioxane (2 ml) into flask #2. After transferring the solution of flask #1 to flask #2, the mixture was heated at reflux for 2 h. Workup as described for 9a left a crude solid that was triturated in 2‐propanol/dichloromethane and collected to give 9g (55 mg, 78%) as a deep yellow solid: 1 H NMR (dimethyl sulfoxide‐ d 6 ) δ 10.70 (s, 1H, NH), 8.89 (s, 1H, pyr H‐2), 8.21 (d, J = 12.5 Hz, 2H, pyr H‐4, H‐6), 7.49–7.27 (m, 4H, Ph‐F 2 H‐2, H‐5, H‐6, pyr H‐5), 5.45 (s, 2H, ‐CH 2 Ph‐F 2 ), 3.33 (s, 3H, NCH 3 ); MS m/z 398.0 (M + H).…”

2-(Azolyl)anilines: methods of synthesis, cyclocondensations, and biological properties

“…The resulting (2-nitrophenyl)-azoles 18 and 19 were converted into the corresponding heterylanilines 20 and 21 via palladium-catalyzed reduction with quantitative yields. Janjic et al 4 obtained (2E)-3-(dimethylamino)-1-(2-nitrophenyl)prop-2-en-1-one (16) by interaction of 2'-nitroacetophenone (14) with N,N'-dimethylformamide dimethyl acetal (DMFDMA). Compound 16 interacting with alkylor arylhydrazines formed 1-substituted 5-(2-nitrophenyl)-1H-pyrazoles 22 in 53-97% yield.…”

Design and development of novel Co‐MOF nanostructures as an excellent catalyst for alcohol oxidation and Henry reaction, with a potential antibacterial activity

“…[34,35] The product of Henry reaction, β-nitroalkanols, could be readily transformed into beneficial synthons for the development of various natural products and pharmaceutically urgent structural scaffolds. [38][39][40] Therefore, for developing of the Henry reaction have made considerable efforts using homogeneous [41][42][43] and heterogeneous [44][45][46][47] catalysts. These building blocks have many applications in synthetic chemistry for the complex molecules construction.…”

“…These building blocks have many applications in synthetic chemistry for the complex molecules construction. [38][39][40] Therefore, for developing of the Henry reaction have made considerable efforts using homogeneous [41][42][43] and heterogeneous [44][45][46][47] catalysts. Among the studies have reported for heterogeneous-catalyzed Henty reaction until now, few reports exist about MOFs that catalyse this reaction.…”