Synthesis and biological properties of new derivatives of 2-arylpyrrolidinecarbonitriles and pyrrolidinecarboxamides

Controllable Lewis Base Catalyzed Michael Addition of α-Amino­nitriles to Activated Alkenes: Facile Synthesis of Functionalized γ-Amino Acid Esters and γ-Lactams

“…In contrast, when the reaction was performed with PBu 3 as catalyst, lactam 4a was produced dominantly in high yield. However, PPh 3 did not display any reactivity towards this transformation (entries 5,6). Further survey indicated that this LB catalyzed controllable reaction was strongly affected by solvent.…”

“…Purification by silica gel column chromatography (PE/EtOAc 6:1) to afford 3a (55 mg, 94%) as a white solid; mp 120.2-121.4 °C. 1 H NMR (500 MHz, CDCl 3 ):  = 7.58 (d, J = 7.4 Hz, 2 H), 7.37 (m, 3 H), 7.09 (t, J = 7.9 Hz, 2 H), 6.77 (t, J = 7.3 Hz, 1 H), 6 57, 142.11, 137.54, 129.44, 129.15, 129.00, 125.66, 124.70, 119.51, 116.81, 61.29, 52.39, 39.19, 29.54 19, 154.07, 138.01, 137.16, 129.30, 129.02, 126.01, 120.01, 118.25, 114.59, 62.20, 55.63, 52.24, 39.13, 29.49…”

“…NMR (300 MHz, CDCl3): δ = 7.48 (dd, J = 1.8, 0.8 Hz, 1H),6.94 -6.80 (m, 4H), 6.47 (dd, J = 3.4, 0.8 Hz, 1H), 6.33 (dd, J = 3.4, 1.9 Hz, 1H),3.77 (s, 3H), 2.97 -2.81 (m, 3H), 2.74 -2.61 (m, 1H). 13 C NMR (126 MHz, CDCl3): δ = 173.78, 159.79, 147.27, 144.39, 129.26, 127.31, 117.94, 114.78, 112.01, 111.15, 61.98, 55.48, 31.78, 29.43.…”

Synthesis and X-ray analysis of 2-aryl-4-chloropyrrolidine-2-carbonitrile derivatives

“…A mixture of 2 g (10 mmol) of 2-anilino-2-phenylacetonitrile (1) [16] and 1.05 g (10 mmol) of triethylamine in 30 mL of acetone was cooled to 0-5°C, 1.6 g (10 mmol) of 2,3-dichloropropanoyl chloride was added, and the mixture was stirred for 30 min at room temperature. The solvent was distilled off, the residue was treated with 50 mL of diethyl ether, and the extract was washed with dilute aqueous HCl and water, dried over Na 2 SO 4 , and evaporated.…”

“…In the present work we used this procedure for the preparation of 4-chloro-5-oxo-1,2-diphenylpyrrolidine-2-carbonitrile 3 (Scheme 1). For this purpose, 2-anilino-2-phenylacetonitrile (1) [16] was acylated with 2,3-dichloropropanoyl chloride, and the subsequent intramolecular cyclization of amide 2 under conditions of phase-transfer catalysis afforded compound 3. The phase-transfer catalyst was benzyl(triethyl)ammonium chloride (BTEAC).…”