Supporting Information. A catalyst-free multicomponent domino sequence for the. diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-
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1 Supporting Information for A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3- (arylamino)allyl]chromen-4-ones Pitchaimani Prasanna 1, Pethaiah Gunasekaran 1, Subbu Perumal* 1 and J. Carlos Menéndez* 2 Address: 1 Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai , Tamilnadu, India and 2 Departamento de Química Orgánica and Farmacéutica, Facultad de Farmacia, Universidad Complutense, Madrid, Spain Subbu Perumal - subbu.perum@gmail.com; J. Carlos Menéndez - josecm@farm.ucm.es *Corresponding author Experimental details, full characterization data, detailed structural characterization of compound 5h and copies of the spectra of all compounds S1
2 1. Experimental details and full characterization data General experimental methods. Melting points were measured in open capillary tubes and are uncorrected. The 1 H NMR, 13 C NMR, DEPT, H,H-COSY, C,H-COSY and HMBC spectra were recorded on a Bruker (Avance) 300 MHz NMR instrument using TMS as internal standard and CDCl 3 as solvent. Standard Bruker software was used throughout. Chemical shifts are given in parts per million (δ-scale) and the coupling constants are given in Hertz. Silica gel-g plates (Merck) were used for TLC analysis with a mixture of petroleum ether (60 80 C) and ethyl acetate as eluent. Elemental analyses were performed on a Perkin Elmer 2400 Series II Elemental CHNS analyzer. General procedure for the synthesis of (E)-3-(2-arylcarbonyl-3-(arylamino)allyl)-4Hchromen-4-one 5a 5p. A mixture of 3-formylchromone (1, 1 mmol), enaminone 2 (1 mmol) and aniline 3 (1 mmol) in DMF (5 ml) was heated at 130 C for 6 7 h. The reaction progress was monitored by thin-layer chromatography. After completion of the reaction, the solvent was removed and the product was purified by column chromatography using petroleum ether ethyl acetate mixture (4:1 v/v) as eluent to afford (E)-3-(2-arylcarbonyl-3- (arylamino)allyl)-4h-chromen-4-ones 5. (E)-3-(2-Benzoyl-3-(p-tolylamino)allyl)-4H-chromen-4-one (5a): Isolated yield g (85%); Colorless solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 2.28 (s, 3H), 3.71 (s, 2H), 6.92 (d, J = 8.4 Hz, 2H), 7.08 (d, J = 8.1 Hz, 2H), (m, 4H), (m, 4H), (m, 1H), 8.31 (d, J = 7.8 Hz, 1H), 8.52 (s, 1H), 9.93 (d, J = 12.6 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.1, 20.6, 113.3, 115.8, 118.3, 123.7, 123.9, 125.0, 125.9, 128.0, 128.5, 129.8, 130.1, 132.3, 133.7, 138.9, 140.9, 146.6, 156.2, 156.7, 179.8, 195.0; HRMS (ESI) calcd for C 26 H 20 NO 3 [M - H] ; found Anal. Calcd for C 26 H 21 NO 3 : C, 78.97; H, 5.35; N, Found: C, 79.02; H, 5.29; N, S2
3 (E)-3-(2-(4-Chlorobenzoyl)-3-(p-tolylamino)allyl)-4H-chromen-4-one (5b): Isolated yield g (87%); Colorless solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 2.30 (s, 3H), 3.69 (s, 2H), 6.93 (d, J = 8.4 Hz, 2H), 7.10 (d, J = 8.1 Hz, 2H), (m, 2H), (m, 4H), 7.51 (s, 1H), 7.69 (td, J = 9 Hz, 1.8 Hz, 1H), 8.30 (dd, J = 6.0 Hz, 1.5 Hz, 1H), 8.50 (s, 1H), 10.0 (d, J = 12.6 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.2, 20.7, 113.2, 115.9, 118.3, 123.6, 123.7, 125.1, 125.9, 128.3, 129.9, 130.1, 132.6, 133.8, 136.0, 138.7, 139.3, 146.6, 156.1, 156.7, 179.8, 193.6; HRMS (ESI) calcd for C 26 H 19 ClNO 3 [M - H] ; found Anal. Calcd for C 26 H 20 ClNO 3 : C, 72.64; H, 4.69; N, Found: C, 72.77; H, 4.77; N, (E)-3-(2-(3-Nitrobenzoyl)-3-(p-tolylamino)allyl)-4H-chromen-4-one (5c): Isolated yield g (90%); Yellow solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 2.32 (s, 3H), 3.72 (s, 2H), 6.93 (d, J = 8.4 Hz, 2H), 7.10 (d, J = 8.1 Hz, 2H), (m, 3H), 7.59 (d, J = 8.0 Hz, 1H), (m, 1H), 7.81 (d, J = 7.5 Hz, 1H), (m, 3H), 8.51 (s, 1H), 10.2 (d, J = 12.6 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.1, 20.7, 113.0, 116.2, 118.4, 123.3, 123.6, 123.7, 124.4, 125.2, 125.9, 129.2, 130.2, 133.1, 133.9, 134.1, 138.4, 142.5, 147.3, 148.0, 156.1, 156.7, 179.9, 191.8; HRMS (ESI) calcd for C 26 H 19 N 2 O 5 [M - H] ; found Anal. Calcd for C 26 H 20 N 2 O 5 : C, 70.90; H, 4.58; N, Found: C, 70.84; H, 4.62; N, (E)-3-(2-Benzoyl-3-(4-methoxyphenylamino)allyl)-4H-chromen-4-one (5d): Isolated yield g (89%); Colorless solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 3.71 (s, 2H), 3.77 (s, 3H), 6.83 (d, J = 9.0 Hz, 2H), 6.96 (d, J = 8.7 Hz, 2H), (m, 4H), (m, 4H), (m, 1H), (m, 1H), 8.53 (s, 1H), 9.90 (d, J = 12.6 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.1, 55.6, 112.9, 115.0, 117.2, 118.3, 123.7, 123.9, 125.0, 125.8, 128.0, 128.4, 129.7, 133.7, 135.0, 141.0, 147.0, 155.7, 156.2, 156.7, 179.8, 194.8; HRMS (ESI) calcd for C 26 H 20 NO 4 [M - H] ; found S3
4 Anal. Calcd for C 26 H 21 NO 4 : C, 75.90; H, 5.14; N, Found: C, 75.79; H, 5.05; N, (E)-3-(2-(4-Chlorobenzoyl)-3-(4-methoxyphenylamino)allyl)-4H-chromen-4-one (5e): Isolated yield g (91%); Colorless solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 3.69 (s, 2H), 3.78 (s, 3H), (m, 2H), (m, 2H), (m, 2H), (m, 4H), 7.50 (d, J = 8.4 Hz, 1H), (td, J = 7.5 Hz, 1.7 Hz, 1H), 8.30 (dd, J = 6.0 Hz, 1.5 Hz, 1H), 8.50 (s, 1H), 9.97 (d, J = 12.3 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.2, 55.6, 112.8, 115.1, 117.3, 118.4, 123.7, 123.8, 125.1, 125.8, 128.3, 129.8, 133.8, 134.8, 135.9, 139.4, 147.1, 155.9, 156.2, 156.7, 179.9, 193.4; HRMS (ESI) calcd for C 26 H 19 ClNO 4 [M - H] ; found Anal. Calcd for C 26 H 20 ClNO 4 : C, 70.03; H, 4.52; N, Found: C, 69.91; H, 4.56; N, (E)-3-(3-(4-Methoxyphenylamino)-2-(3-nitrobenzoyl)allyl)-4H-chromen-4-one (5f): Isolated yield g (94%); Orange solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 3.72 (s, 2H), 3.77 (s, 3H), 6.85 (d, J = 8.7 Hz, 2H), 6.98 (d, J = 8.7 Hz, 2H), (m, 2H), 7.52 (d, J = 8.4 Hz, 1H), 7.59 (t, J = 8.0 Hz, 1H), 7.71 (t, J = 7.7 Hz, 1H), 7.82 (d, J = 7.5 Hz, 1H), (m, 3H), 8.51 (s, 1H), (d, J = 12.6 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.1, 55.6, 112.6, 115.1, 117.6, 118.4, 123.2, 123.5, 123.6, 124.3, 125.2, 125.8, 129.2, 133.9, 134.1, 134.5, 142.6, 147.7, 148.0, 156.1, 156.2, 156.7, 179.9, 191.6; HRMS (ESI) calcd for C 26 H 19 N 2 O 6 [M - H] ; found Anal. Calcd for C 26 H 20 N 2 O 6 : C, 68.42; H, 4.42; N, Found: C, 68.50; H, 4.38; N, (E)-3-(2-(4-Chlorobenzoyl)-3-(4-chlorophenylamino)allyl)-4H-chromen-4-one (5g): Isolated yield g (86%); Colorless solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 3.69 (s, 2H), (m, 2H), (m, 2H), (m, 3H), (m, 3H), 7.51 (d, J = 8.4 Hz, 1H), 7.70 (td, J = 7.5 Hz, 1.8 Hz, 1H), 8.30 (dd, J = 9 Hz, 1.5 Hz, 1H), 8.49 (s, 1H), (d, J = 12.3 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.3, S4
5 114.2, 117.0, 118.4, 123.5, 123.6, 125.2, 125.8, 127.8, 128.4, 129.7, 129.9, 133.9, 136.3, 139.0, 139.9, 145.7, 156.3, 156.7, 179.9, 193.8; HRMS (ESI) calcd for C 25 H 16 Cl 2 NO 3 [M - H] ; found Anal. Calcd for C 25 H 17 Cl 2 NO 3 : C, 66.68; H, 3.81; N, Found: C, 66.81; H, 3.74; N, (E)-3-(3-(4-Chlorophenylamino)-2-(4-methylbenzoyl)allyl)-4H-chromen-4-one (5h): Isolated yield g (84%); Colorless solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 2.40 (s, 3H), 3.70 (s, 2H), 6.95 (d, J = 8.7 Hz, 2H), (m, 4H), (m, 3H), (m, 2H), 7.69 (t, J = 7.1 Hz, 1H), 8.30 (d, J = 7.2 Hz, 1H), 8.51 (s, 1H), (d, J = 12.3 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.4, 21.4, 114.4, 116.8, 118.4, 123.7, 125.1, 125.8, 127.4, 128.6, 128.8, 129.5, 133.8, 137.7, 140.1, 140.4, 145.3, 156.3, 156.7, 179.9, 195.2; HRMS (ESI) calcd for C 26 H 19 ClNO 3 [M - H] ; found Anal. Calcd for C 26 H 20 ClNO 3 : C, 72.64; H, 4.69; N, Found: C, 72.57; H, 4.75; N, (E)-3-(3-(4-Chlorophenylamino)-2-(4-methoxybenzoyl)allyl)-4H-chromen-4-one (5i): Isolated yield g (82%); Colorless solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 3.70 (s, 2H), 3.86 (s, 3H), 6.91 (d, J = 8.7 Hz, 2H), 6.96 (d, J = 8.7 Hz, 2H), (m, 2H), (m, 5H), (m, 1H), 8.30 (dd, J = 6.0 Hz, 1.2 Hz, 1H), 8.51 (s, 1H), (d, J = 12.0 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.6, 55.4, 113.5, 114.3, 116.8, 118.4, 123.7, 125.1, 125.8, 127.3, 129.6, 130.5, 133.8, 140.2, 144.8, 156.3, 156.7, 161.5, 179.9, 194.5; HRMS (ESI) calcd for C 26 H 19 ClNO 4 [M - H] ; found Anal. Calcd for C 26 H 20 ClNO 4 : C, 70.03; H, 4.52; N, Found: C, 69.98; H, 4.59; N, (E)-3-(3-(4-Chlorophenylamino)-2-(3-nitrobenzoyl)allyl)-4H-chromen-4-one (5j): Isolated yield g (87%); Yellow solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 3.72 (s, 2H), 6.96 (d, J = 8.7 Hz, 2H), 7.25 (d, J = 8.7 Hz, 2H), (m, 3H), S5
6 7.61 (t, J = 7.8 Hz, 1H), (m, 1H), 7.82 (d, J = 7.5 Hz, 1H), (m, 3H), 8.51 (s, 1H), (d, J = 12.3 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.3, 114.1, 117.2, 118.4, 123.2, 123.3, 123.6, 124.6, 125.3, 125.8, 128.3, 129.3, 129.7, 134.0, 139.6, 142.2, 146.4, 148.1, 156.3, 156.7, 180.0, 192.1; HRMS: calcd. for C 25 H 16 ClN 2 O 5 [M - H] ; found Anal. Calcd for C 25 H 17 ClN 2 O 5 : C, 65.15; H, 3.72; N, Found: C, 65.24; H, 3.68; N, (E)-3-(2-Benzoyl-3-(4-bromophenylamino)allyl)-4H-chromen-4-one (5k): Isolated yield g (80%); Colorless solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 3.70 (s, 2H), 6.89 (d, J = 8.7 Hz, 2H), (m, 3H), (m, 3H), (m, 4H), (m, 1H), 8.30 (dd, J = 6.0 Hz, 1.5 Hz, 1H), 8.52 (s, 1H), (d, J = 12.3 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.3, 114.5, 114.9, 117.3, 118.4, 123.6, 125.2, 125.8, 128.1, 128.4, 130.1, 132.5, 133.9, 140.5, 140.6, 145.5, 156.3, 156.7, 179.9, 195.2; HRMS (ESI) calcd for C 25 H 17 BrNO 3 [M - H] ; found Anal. Calcd for C 25 H 18 BrNO 3 : C, 65.23; H, 3.94; N, Found: C, 65.35; H, 4.01; N, (E)-3-(3-(4-Bromophenylamino)-2-(4-methylbenzoyl)allyl)-4H-chromen-4-one (5l): Isolated yield g (81%); Colorless solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 2.40 (s, 3H), 3.70 (s, 2H), 6.90 (d, J = 8.7 Hz, 2H), 7.21 (d, J = 8.1 Hz, 2H), (m, 3H), (m, 4H), 7.69 (dd, J = 7.5 Hz, 1.5 Hz, 1H), 8.30 (dd, J = 8.1 Hz, 1.8 Hz, 1H), 8.51 (s, 1H), (d, J = 12.0 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.4, 21.4, 114.5, 114.7, 117.2, 118.4, 123.6, 125.1, 125.8, 128.6, 128.8, 132.5, 133.8, 137.7, 140.4, 140.6, 145.1, 156.4, 156.7, 179.9, 195.2; HRMS (ESI) calcd for C 26 H 19 BrNO 3 [M - H] ; found Anal. Calcd for C 26 H 20 BrNO 3 : C, 65.83; H, 4.25; N, Found: C, 65.70; H, 4.34; N, S6
7 (E)-3-(3-(4-Fluorophenylamino)-2-(4-methylbenzoyl)allyl)-4H-chromen-4-one (5m): Isolated yield g (83%); Colorless solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 2.40 (s, 3H), 3.70 (s, 2H), (m, 4H), 7.21 (d, J = 7.8 Hz, 2H), 7.26 (s, 1H), (m, 2H), (m, 2H), 7.70 (td, J = 7.5 Hz, 1.8 Hz, 1H), 8.30 (dd, J = 6.0 Hz, 1.4 Hz, 1H), 8.52 (s, 1H), 9.97 (d, J = 12.3 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.3, 21.4, 113.8, 116.1, 116.4, 116.9, 117.0, 118.4, 123.7, 123.8, 125.1, 125.8, 128.6, 128.8, 133.8, 137.7, 137.8, 137.9, 140.2, 146.1, 156.3, 156.7, 157.1, 160.3, 179.9, 195.1; HRMS (ESI) calcd for C 26 H 19 FNO 3 [M - H] ; found Anal. Calcd for C 26 H 20 FNO 3 : C, 75.53; H, 4.88; N, Found: C, 75.65; H, 4.78; N, (E)-3-(2-(4-Methylbenzoyl)-3-(3-nitrophenylamino)allyl)-4H-chromen-4-one (5n): Isolated yield g (78%); Yellow solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 2.33 (s, 3H), 3.63 (s, 2H), 7.15 (d, J = 6.6 Hz, 2H), (m, 7H), (m, 3H), 8.24 (d, J = 7.2 Hz, 1H), 8.43 (s, 1H), (d, J = 11.1 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.7, 21.4, 109.9, 115.9, 116.5, 118.3, 121.3, 123.3, 123.5, 125.2, 125.8, 128.7, 128.9, 130.3, 133.9, 137.3, 140.9, 142.9, 144.0, 149.4, 156.5, 156.6, 180.0, 195.4; HRMS (ESI) calcd for C 26 H 19 N 2 O 5 [M - H] ; found Anal. Calcd for C 26 H 20 N 2 O 5 : C, 70.90; H, 4.58; N, Found: C, 71.03; H, 4.68; N, (E)-3-(2-(4-Chlorobenzoyl)-3-(phenylamino)allyl)-4H-chromen-4-one (5o): Isolated yield g (86%); Colorless solid. m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 3.71 (s, 2H), (m, 3H), (m, 2H), (m, 2H), (m, 5H), (m, 1H), 8.31 (d, J = 7.8 Hz, 1H), 8.50 (s, 1H), (d, J = 12.3 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.2, 113.7, 115.9, 118.4, 122.9, 123.7, 125.1, 125.9, 128.4, 129.7, 129.9, 133.8, 136.1, 139.2, 141.1, 146.2, 156.2, 156.7, 179.8, 193.8; HRMS (ESI) calcd for C 25 H 17 ClNO 3 [M - H] ; found Anal. Calcd for C 25 H 18 ClNO 3 : C, 72.20; H, 4.36; N, Found: C, 72.09; H, 4.24; N, S7
8 (E)-3-(2-(3-Nitrobenzoyl)-3-(phenylamino)allyl)-4H-chromen-4-one (5p): Isolated yield g (88%); Yellow solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 3.73 (s, 2H), (m, 3H), (m, 2H), (m, 2H), 7.52 (d, J = 8.4 Hz, 1H), 7.60 (t, J = 8.0 Hz, 1H), 7.71 (td, J = 7.5 Hz, 1.5 Hz, 1H), 7.82 (d, J = 7.8 Hz, 1H), (m, 3H), 8.51 (s, 1H), (d, J = 12.6 Hz, 1H); 13 C NMR (75 MHz, CDCl 3, δ ppm): 20.2, 113.5, 116.1, 118.4, 123.2, 123.3, 123.5, 123.6, 124.5, 125.2, 125.9, 129.3, 129.7, 133.9, 134.1, 140.8, 142.4, 146.9, 148.1, 156.2, 156.7, 179.9, 192.0; HRMS (ESI) calcd for C 25 H 17 N 2 O 5 [M - H] ; found Anal. Calcd for C 25 H 18 N 2 O 5 : C, 70.42; H, 4.25; N, Found: C, 70.34; H, 4.31; N, General procedure for the isolation of intermediates 4. A mixture of the suitable enaminone 2 (1 mmol) and aniline 3 (1 mmol) in DMF (5 ml) was heated at 130 C for 3 h. The reaction progress was monitored by thin-layer chromatography. After completion of the reaction, the solvent was removed and the product was purified by column chromatography using a petroleum ether ethyl acetate mixture (4:1 v/v) as eluent. (E)-3-(4-methoxyphenylamino)-1-(3-nitrophenyl)prop-2-en-1-one: Isolated yield g (94%); Orange solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 3.80 (s, 3H), 5.98 (d, J = 7.5 Hz, 1H), 6.90 (d, J = 8.70 Hz, 2H), 7.08 (d, J = 8.70 Hz, 2H), (m, 1H), (m, 1H), (m, 2H), 8.72 (s, 1H), (d, J = 12.2 Hz, NH); 13 C NMR (75 MHz, CDCl 3, δ ppm): 55.5, 92.3, 115.1, 118.3, 122.1, 125.5, 129.4, 132.8, 133.2, 140.9, 147.2, 148.4, 156.9, 187.1; Anal. Calcd for C 16 H 14 N 2 O 4 : C, 64.42; H, 4.73; N, Found: C, 64.55; H, 4.80; N, (E)-1-phenyl-3-(phenylamino)prop-2-en-1-one: Isolated yield g (90%); Yellow solid; m.p o C. 1 H NMR (300 MHz, CDCl 3, δ ppm): 6.02 (d, J = 7.8 Hz, 1H), (m, 3H), (m, 2H), (m, 2H), (m, 2H), (m, 2H), S8
9 12.15 (d, J = 11.9 Hz, NH); 13 C NMR (75 MHz, CDCl 3, δ ppm): 93.7, 116.3, 123.6, 127.3, 128.3, 128.4, 129.7, 131.5, 131.6, 139.2, 139.3, 140.2, 140.3, 144.9, 191.0; Anal. Calcd for C 15 H 13 NO: C, 80.69; H, 5.87; N, Found: C, 80.78; H, 5.83; N, X-Ray data for compound 5h (CCDC number ) Single Crystal X-Ray structure of compound 5h Crystal data of 5h Empirical formula C 26 H 20 ClN 1 O 3 Formula weight Temperature 298(2) K Wavelength Å Crystal system Monoclinic Space group P 21/n Unit cell dimensions a = (15) Å α= 90. b = (8) Å β= (2). c = (3) Å = 90. Volume (4) Å 3 Z 4 Density (calculated) kg/m 3 Absorption coefficient mm -1 F(000) 896 Crystal size 0.24 x 0.22 x 0.17 mm 3 Theta range for data collection 2.0 to Index ranges -17 h 17, -9 k 9, -28 l 28 Reflections collected/ unique 23517/ 5204 [R(int) = ] Completeness to theta = % S9
10 Absorption correction Psi scan Refinement method Full-matrix least-squares on F2 Data / restraints / parameters 5036 / 0 / 280 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.å NMR assignments of compound 5h The 1 H NMR spectrum of 5h gives a singlet at 3.70 ppm for the methylenic hydrogens (1- CH 2 ), which show a C,H-COSY correlation with the carbon signal at 20.4 ppm. These hydrogens also show HMBCs with C-2', C-3', C-4', C-1'', C-2 and C-3 at 156.3, 123.7, 179.9, 195.2, and ppm respectively. The singlet at 8.51 ppm assignable to H- 2' shows (i) a C,H-COSY correlation with the carbon signal at ppm and (ii) HMBCs with C-1, C-3' and C-4' at 20.4, and ppm respectively. The NH hydrogen appears as a doublet at 10.4 ppm (J = 12.3 Hz) , d, J = 12.3 Hz, 1H 3.70, s, 2H O O 20.4 HN H H H O , s, 1H h H Cl merged ( ) CH 3 Cl 6' 5' 4' 4a' O 3' H 1 HN H 2 H 7' 8' 8a' O 2' H O 3 Selected 1 H and 13 C chemical shifts and HMBC correlations of 5h CH 3 S10
11 4. Copies of spectra Figure 1. 1 H NMR Spectrum of 5a (CDCl 3 ) Figure C NMR Spectrum of 5a (CDCl 3 ) S11
12 Figure 3. HRMS measurement for 5a Figure 4. 1 H NMR Spectrum of 5b (CDCl 3 ) S12
13 Figure C NMR Spectrum of 5b (CDCl 3 ) Figure 6. HRMS measurement for 5b S13
14 Figure 7. 1 H NMR Spectrum of 5c (CDCl 3 ) Figure C NMR Spectrum of 5c (CDCl 3 ) S14
15 Figure 9. HRMS measurement for 5c Figure H NMR Spectrum of 5d (CDCl 3 ) S15
16 Figure C NMR Spectrum of 5d (CDCl 3 ) Figure 12. HRMS measurement for 5d S16
17 Figure H NMR Spectrum of 5e (CDCl 3 ) Figure C NMR Spectrum of 5e (CDCl 3 ) S17
18 Figure 15. HRMS measurement for 5e Figure H NMR Spectrum of 5f (CDCl 3 ) S18
19 Figure C NMR Spectrum of 5f (CDCl 3 ) Figure 18.HRMS measurement for 5f S19
20 Figure H NMR Spectrum of 5g (CDCl 3 ) Figure C NMR Spectrum of 5g (CDCl 3 ) S20
21 Figure 21. HRMS measurement for 5g Figure H NMR Spectrum of 5h (CDCl 3 ) S21
22 Figure C NMR Spectrum of 5h (CDCl 3 ) Figure 24. DEPT NMR Spectrum of 5h (CDCl 3 ) S22
23 Figure 25. H,H-COSY Spectrum of 5h (CDCl 3 ) Figure 26. HMBC Spectrum of 5h (CDCl 3 ) S23
24 Figure 27. C,H-COSY Spectrum of 5h (CDCl 3 ) Figure 28. HRMS measurement for 5h S24
25 Figure H NMR Spectrum of 5i (CDCl 3 ) Figure C NMR Spectrum of 5i (CDCl 3 ) S25
26 Figure 31. HRMS measurement for 5i Figure H NMR Spectrum of 5j (CDCl 3 ) S26
27 Figure C NMR Spectrum of 5j (CDCl 3 ) Figure 34. HRMS measurement for 5j S27
28 Figure H NMR Spectrum of 5k (CDCl 3 ) Figure C NMR Spectrum of 5k (CDCl 3 ) S28
29 Figure 37. HRMS measurement for 5k Figure H NMR Spectrum of 5l (CDCl 3 ) S29
30 Figure C NMR Spectrum of 5l (CDCl 3 ) Figure 40. HRMS measurement for 5l S30
31 Figure H NMR Spectrum of 5m (CDCl 3 ) Figure C NMR Spectrum of 5m (CDCl 3 ) S31
32 Figure 43. HRMS measurement for 5m Figure H NMR Spectrum of 5n (CDCl 3 ) S32
33 Figure C NMR Spectrum of 5n (CDCl 3 ) Figure 46.HRMS measurement for 5n S33
34 Figure H NMR Spectrum of 5o (CDCl 3 ) Figure C NMR Spectrum of 5o (CDCl 3 ) S34
35 Figure 49. HRMS measurement for 5o Figure H NMR Spectrum of 5p (CDCl 3 ) S35
36 Figure C NMR Spectrum of 5p (CDCl 3 ) Figure 52. HRMS measurement for 5p S36
37 Deuteration experiment A mixture of 3-formylchromone (1, 0.1 mmol), enaminone 2 (0.1 mmol) and aniline 3 (0.1 mmol) in DMF-d 7 (1 ml) was heated to reflux for 6 7 h. The reaction progress was monitored by thin-layer chromatography. After completion of the reaction, the solvent was removed and the product was purified by column chromatography using a petroleum ether ethyl acetate mixture (4:1 v/v) as eluent to afford compounds 4 in 83% of yield. 1 H NMR spectrum S37
38 1 H NMR spectrum 13 C NMR spectrum S38
39 13 C NMR spectrum S39
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