Catalyst-free, one pot and three-component synthesis of 4′-phenyl-1′H-spiro[indoline-3,2′-quinazolin]-2-ones and 2,4-diphenyl-1,2-dihydroquinazolines

Skeletal Transformation of Oxindoles into Quinolinones Enabled by Synergistic Copper/Iminium Catalysis

“…All oxime esters and isatin-derived enals − were synthesized according to the literature procedures. All of the starting materials were known.…”

Investigation of N,N′‐Disulfopiperazinium Chlorometallates of Fe(III), Ni(II) and Co(II) as Hybrid Catalysts for the Synthesis of 1,2‐Dihydroquinazoline Derivatives

“…2‐(4‐chlorophenyl)‐4‐phenyl‐1,2‐dihydroquinazoline [44,45,70] ( 6 a ) : Greenish yellow solid; FT‐IR (KBr) ν cm −1 : 3390, 3243, 3063, 2924, 2249, 1613, 1561, 1485, 1338, 1095, 907, 691 and 539; 1 H NMR (CDCl 3 , 400 MHz): δ 7.56–7.51 (m, 4H), 7.44–7.39 (m, 3H), 7.35 (d, J =8.0 Hz, 2H), 7.25 (t, J =8.0 Hz, 1H), 7.17 (d, J =8.0 Hz, 1H), 6.73 (t, J =8.0 Hz, 1H), 6.67 (d, J =8.0 Hz, 1H), 5.89 (s, 1H), 4.28 (s, 1H); 13 C NMR (CDCl 3 , 100 MHz): δ 166.12, 146.69, 141.12, 138.01, 134.20, 129.28, 128.91, 128.82, 128.29, 118.58, 117.95, 114.45, 100.00, 71.96; CHN analysis (Mol. Formula C 20 H 15 ClN 2 ): calculated (%) C 75.35, H 4.74, N 8.79; Found (%) C 75.32, H 4.72, N 8.73.…”

“…2‐(3‐nitrophenyl)‐4‐phenyl‐1,2‐dihydroquinazoline [45,70] ( 6 e ) : Yellow solid; FT‐IR (KBr) ν cm −1 : 3436, 2921, 2254, 1622, 1529, 1464, 1342, 1076, 905, 697 and 532; 1 H NMR (CDCl 3 , 400 MHz): δ 8.46–8.45 (m, 1H), 8.17 (d, J =8.0 Hz, 1H), 7.96–7.95 (m, 1H), 7.62 (m, 1H), 7.56–7.53 (m, 2H), 7.45–7.41 (m, 3H), 7.30–7.28 (m, 1H), 7.18 (d, J =8.0 Hz, 1H), 6.77–6.70 (m, 2H), 6.05 (s, 1H), 4.24 (s, 1H); 13 C NMR (CDCl 3 , 100 MHz): δ 166.70, 148.43, 146.34, 144.71, 137.67, 133.78, 130.29, 129.47, 128.33, 123.37, 122.55, 118.99, 117.99, 114.73, 71.53; CHN analysis (Mol. Formula C 20 H 15 N 3 O 2 ): calculated (%) C 72.94, H 4.59, N 12.76; Found (%) C 72.90, H 4.51, N 12.73.…”

“…2‐(4‐methoxyphenyl)‐4‐phenyl‐1,2‐dihydroquinazoline [45,70] ( 6 h ) : Yellow solid; FT‐IR (KBr) ν cm −1 : 3449, 3065, 2936, 2346, 1612, 1513, 1448, 1314, 1028, 751, 700, 537; 1 H NMR (CDCl 3 , 400 MHz): δ 8.65 (d, J =8.0 Hz, 1H), 7.59–7.54 (m, 2H), 7.51–7.49 (m, 2H), 7.43–7.39 (m, 1H), 7.24–7.22 (m, 1H), 7.15 (d, J =8.0 Hz, 1H), 7.04–7.01 (m, 1H), 6.91 (d, J =8.0 Hz, 2H), 6.70 (t, J =8.0 Hz, 1H), 6.66 (d, J =8.0 Hz, 1H), 5.89 (s, 1H), 4.25 (s, 1H), 3.79 (s, 3H); 13 C NMR (CDCl 3 , 100 MHz): δ 168.33, 161.85, 160.17, 158.92, 152.17, 151.67, 140.56, 137.86, 135.62, 130.61, 130.26, 129.15, 128.59, 128.13, 121.51, 117.53, 114.23, 112.08, 55.45; CHN analysis (Mol. Formula C 21 H 18 N 2 O): calculated (%) C 80.23, H 5.77, N 8.91; Found (%) C 80.21, H 5.71, N 8.85.…”

Stereoselective Synthesis of Spiro-Decalin Oxindole Derivatives via Sequential Organocatalytic Michael–Domino Michael/Aldol Reaction

“…The product was isolated after flash chromatography on silica gel. Unless otherwise stated, the compounds were prepared following this procedure and all the analytical data were in accordance with the literature reports. , …”