Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 206 Supporting information For An efficient and green method for regio- and chemo-selective Friedel Crafts acylations using a deep eutectic solvent ([CholineCl][ZnCl 2 ] 3 ) Table of contents Section Spectral data S-S2 Section 2 References S2-S Section 3 NMR spectra S4-S44 S
Section. Spectral data [CholineCl][ZnCl 2 ] 3 IR ν max 3543, 69, 475 cm -. H-NMR (300 MHz, DMS-d6): δ 5.23 (s, H), 3.8-3.78 (m, 2H), 3.34-3.32 (m, 2H), 3.04 (s, 9H). C-NMR (75 MHz, DMS-d6): δ 67.8, 55.9, 54.2, 54., 54.0. HRMS (ESI): [Choline + H] + 05.0504 [ZnCl 3 ] - 70.8356, [Zn 2 Cl 5 ] - 306.6968, [Zn 3 Cl 7 ] - 444.5604 4-Methoxypropiophenone 2 C 2 H 5 Me H NMR (500 MHz, CDCl 3 ): δ 7.87 (d, J = 8.5 Hz, 2H), 6.86 (d, J = 8.5 Hz, 2H), 3.79 (s, 3H), 2.88 (q, J = 7.3 Hz, 2H),.4 (t, J = 7.3 Hz, 3H). C NMR (25 MHz, CDCl 3 ): δ 99.4, 63.3, 0.2, 0.,.7, 55.4, 3.4, 8.4. GC-MS (EI, 70 ev): m/z 64 (M + ). 3-Propionylindole 3 N H H NMR (500 MHz, CDCl 3 ): δ 8.70 (br s, H), 8.4 8.40 (m, H), 7.88 (s, H), 7.43 7.4 (m, H), 7.30 7.28 (m, 2H), 2.93 (q, J = 7.4 Hz, 2H),.28 (t, J = 7.4 Hz, 3H). C NMR (25 MHz, CDCl 3 ): δ 97., 6.3, 0.9, 25.6, 23.7, 22.6, 22.5, 7.9,.4, 33., 9.0. GC MS (EI, 70 ev) m/z = 73 [M + ]. 4-Methoxyacetophenone 4 S2
H 3 C Me H NMR (300 MHz, CDCl 3 ): δ 7.93 (d, J = 9.0 Hz, 2H), 6.93 (d, J = 9.0 Hz, 2H), 3.86 (s, 3H), 2.55 (s, 3H). C NMR (75 MHz, CDCl 3 ) δ 96.7, 63.5, 0.6, 0.3,.7, 55.4, 26.3. GC-MS (EI, 70 ev): m/z 50 (M + ). 4-Methoxybutyrophenone 2 C 3 H 7 Me H NMR (500 MHz, CDCl 3 ): δ 7.92 (d, J = 8.9 Hz, 2H), 6.9 (d, J = 8.9 Hz, 2H), 3.84 (s, 3H), 2.87 (t, J = 7.3 Hz, 2H),.74 (dd, J= 4.7, 7.4 Hz, 2H), 0.98 (t, J = 7.4 Hz, 3H). C NMR (25 MHz, CDCl 3 ) δ 99., 63.3,.0, 0.3,.7, 55.4, 40.2, 8.0,.9. GC-MS (EI, 70 ev): m/z 78 (M + ). 4-Methoxybenzophenone 5 Me H NMR (300 MHz, CDCl 3 ): δ 7.86-7.8 (m, 2H), 7.75 (dd, J = 8.3,.4 Hz, 2H), 7.55 (d, J = 7.5 Hz, H), 7.49-7.44 (m, 2H), 6.96 (d, J = 9.0 Hz, 2H), 3.88 (s, 3H). C NMR (25 MHz, CDCl 3 ) δ 95.6, 63.2, 8.3, 2.6,.9, 0.2, 29.8, 28.2,.6, 55.5. GC-MS (EI, 70 ev): m/z 22 (M + ). 3,4-Dimethoxybenzophenone 5 S3
Me Me H NMR (300 MHz, CDCl 3 ): δ 7.77 (dd, J = 8.4,.4Hz, 2H), 7.49 (s, H), 7.46-7.36 (m, 3H), 6.90 (m, 2H), 3.96 (s, 3H), 3.95 (s, 3H). C NMR (75 MHz, CDCl 3 ) δ 95.6, 53.0, 49.0, 8.3,.9, 0.2, 29.7, 28.2, 25.5, 2., 09.7, 56., 56.0. GC-MS (EI, 70 ev): m/z 242 (M + ). 3,4-Dimethoxypropiophenone 2 C 2 H 5 Me Me H NMR (500 MHz, CDCl 3 ): δ 7.58 (dd, J = 8.4, 2.0 Hz, H), 7.53 (d, J = 2.0 Hz, H), 6.87 (d, J = 8.4 Hz, H), 3.93 (s, 3H), 3.92 (s, 3H), 2.95 (q, J = 7.3 Hz, 2H),.2 (t, J = 7.3 Hz, 3H). C NMR (25 MHz, CDCl 3 ): δ 99.5, 53., 49.0, 0.2, 22.5, 0.2, 0.0, 56.0, 56.0, 3.3, 8.6. GC-MS (EI, 70 ev): m/z 94 (M + ). 2,4-Dimethoxybenzophenone 6 Me Me H NMR (300 MHz, CDCl 3 ): δ 7.77 (dd, J = 8.4,.4 Hz, 2H), 7.49 (s, H), 7.42 (dt, J =.8, 0.6 Hz, H), 7.39 (s, 2H), 6.53 (dd, J = 9.6, 5.3 Hz, 2H), 3.86 (s, 3H), 3.69 (s, 3H). C NMR (75 MHz, CDCl 3 ) δ 95.6, 63.4, 59.6, 8.8, 2.3, 2.2, 29.7, 28.0, 2.5, 04.6, 98.8, 55.6, 55.5. GC-MS (EI, 70 ev): m/z 242 (M + ). 2, 5-Dimethoxybenzophenone 6 S4
Me Me H NMR (300 MHz, CDCl 3 ): δ 7.84-7.80 (m, 2H), 7.57-7.52 (m, H), 7.47-7.38 (m, 2H), 7.0 (dd, J = 9.0, 3.0 Hz, H), 6.92 (dd, J = 6.0, 3.0 Hz, 2H), 3.78 (s, 3H), 3.66 (s, 3H). C NMR (75 MHz, CDCl 3 ) δ 96.2, 53.5, 5.5, 7.6, 3.0, 29.8, 28.2, 7.3, 4.4,., 56.3, 55.8. GC-MS (EI, 70 ev): m/z 242 (M + ). 2, 4, 5-Trimethoxybenzophenone 2 Me Me Me H NMR (500 MHz, CDCl 3 ): δ 7.76 (d, J = 8.2 Hz, 2H), 7.5 (t, J = 6.8 Hz, H), 7.40 (t, J = 7.6 Hz, 2H), 7.02 (s, H), 6.55 (s, H), 3.94 (s, 3H), 3.83 (s, 3H), 3.64 (s, 3H). C NMR (25 MHz, CDCl 3 ): δ 95.5, 53.4, 52.6, 43.3, 9.0, 2.3, 0., 29.5, 28.4, 28.0, 20.,.6, 97.8, 56.6, 56.5, 56.2. GC-MS (EI, 70 ev): m/z 272 (M + ). 2, 4, 6-Trimethylbenzophenone 6 Me Me Me H NMR (500 MHz, CDCl 3 ): δ 7.80 (d, J = 7.2 Hz, 2H), 7.57 (t, J= 7.4 Hz, H), 7.44 (t, J = 7.8 Hz, 2H), 6.90 (s, 2H), 2.33 (s, 3H), 2.08 (s, 6H). C NMR (25 MHz, CDCl 3 ) δ 200.8, 8.5, 7.4, 6.9, 4.2, 3.5, 29.4, 28.8, 28.4, 2.2, 9.4. GC-MS (EI, 70 ev): m/z 223 (M+H). S5
2, 4, 6-Trimethylpropiophenone 2 Me C 2 H 5 Me Me H NMR (500 MHz, CDCl 3 ): δ 6.83 (s, 2H), 2.70 (q, J = 7.3 Hz, 2H), 2.28 (s, 3H), 2.8 (s, 6H),.9 (t, J = 7.3 Hz, 3H). C NMR (25 MHz, CDCl 3 ): δ 2.4, 9.9, 8., 2.4, 28.4, 37.9, 2.0, 9.0, 7.6. GC-MS (EI, 70 ev): m/z 76 (M + ). 2, 4-Dimethylbenzophenone 7 Me Me H NMR (500 MHz, CDCl 3 ): δ 7.77 (dd, J = 8.3,.2 Hz, 2H), 7.54 (t, J = 7.4 Hz, H), 7.42 (m, 2H), 7.2 (d, J = 7.7 Hz, H), 7.09 (s, H), 7.02 (d, J = 7.7 Hz, H), 2.36 (s, 3H), 2.3 (s, 3H). C NMR (25 MHz, CDCl 3 ) δ 98.5, 40.6, 8.3, 7.3, 5.7, 2.8,.9, 0., 29.2, 28.4, 27.5, 25.8, 2.4, 20.. GC-MS (EI, 70 ev): m/z 20 (M + ). 2, 5-Dimethylbenzophenone 7 Me Me H NMR (500 MHz, CDCl 3 ): δ 7.82 7.80 (m, 2H), 7.80 7.56 (m, H), 7.47 7.44 (m, 2H), 7.2 7.7 (m, 2H), 7. (s, H), 2.34 (s, 3H), 2.28 (s, 3H). C NMR (25 MHz, CDCl 3 ) δ 98.9, 8.6, 7.8, 4.8, 3.4, 3.0, 0.9, 0.8, 0., 28.9, 28.4, 2.3, 20.8, 9.5. GC-MS (EI, 70 ev): m/z 20 (M + ). S6
4-Isopropylbenzophenone 6 H NMR (500 MHz, CDCl 3 ): δ 7.85 7.78 (m, 2H), 7.76 (d, J = 8.2 Hz, 2H), 7.58 (t, J = 7.4 Hz, H), 7.48 (t, J = 7.7 Hz, 2H), 7.34 (d, J = 8.2 Hz, 2H), 3.00 (s, H),.30 (t, J = 6.4 Hz, 6H). C NMR (25 MHz, CDCl 3 ): δ 96.2, 54.0, 8.0, 5.3, 2., 0.4, 0.0, 28.2, 26.4, 2.7, 34.3, 24., 23.7. GC-MS (EI, 70 ev) m/z: 224 ([M] + ). 4-Methylthiobenzophenone 6 SMe H NMR (500 MHz, CDCl 3 ): δ 7.75 (m, 4H), 7.57 (t, J = 7.4 Hz, H), 7.47 (t, J = 7.6 Hz, 2H), 7.3 7.27 (m, 2H), 2.53 (s, 3H). C NMR (25 MHz, CDCl 3 ) δ 95.8, 45.3, 7.9, 3.7, 2.2, 0.6, 29.8, 28.3, 24.9, 4.9. GC-MS (EI, 70 ev): m/z 228 (M + ). 3-Acetylindole 8,9 N H H NMR (500 MHz, CDCl 3 ): δ 8.76 (br s, H), 8.40 8.39 (m, H), 7.87 (s, H), 7.43 7.4 (m, H), 7.30 7.29 (m, 2H), 2.56 (s, 3H). C NMR (25 MHz, CDCl 3 ): δ 93.6, 6.4,.4, 25.4, 23.7, 22.7, 22.4, 8.7,.3, 27.6. S7
GC MS (EI, 70 ev): m/z (%) = 59 (50, [M + ]). 3-Butyrylindole 9- N H H NMR (500 MHz, CDCl 3 -d ): δ 8.85 (br s, H), 8.43 8.4 (m, H), 7.88 (d, J = 2.6 Hz, H), 7.43 7.4 (m, H), 7.30 7.28 (m, 2H), 2.86 (t, J = 7.4, 2H),.83 (hext, J = 7.4 Hz, 2H),.03 (t, J = 7.4 Hz, 3H). C NMR (25 MHz, CDCl 3 -d ): δ 96.7, 6.4,., 25.5, 23.7, 22.6, 22.5 8.3,.4, 4.9, 8.6, 4.. GC MS (EI, 70 ev) m/z = 87 [M + ]. 3-Isobutyrylindole 8,9 N H H NMR (300 MHz, DMS-d 6 ): δ.90 (br s, H), 8.34 (s, H), 8.24 8.9 (m, H), 7.48 7.45 (m, H), 7.23 7.4 (m, 2H), 3.45 (hept, J = 6.8 Hz, H),.2 (d, J = 6.8 Hz, 6H). C NMR (75 MHz, DMS-d 6 ): δ 99.4, 6.7, 3.4, 25.7, 22.7, 2.6, 2.5, 4.9, 2.0, 35.8, 9.8. GC MS (EI, 70 ev) m/z = 87 [M + ]. 3-Pivaloylindole 8,9, N H S8
H NMR (300 MHz, DMS-d 6 ): δ.84 (br s, H), 8.34 (s, H), 8.29 8.26 (m, H), 7.46 7.43 (m, H), 7.2 7. (m, 2H),.34 (s, 9H). C NMR (75 MHz, DMS-d 6 ): δ 20., 5.6, 2.4, 27.2, 22.5, 22.0, 2.4, 2.2,.7, 43.4, 28.6. GC MS (EI, 70 ev) m/z = 20 [M + ]. 3-Benzoylindole 8, N H H NMR (500 MHz, CDCl 3 -d ): δ 8.65 (br s, H), 8.43 (dd, J = 6.2, 2.9 Hz, H), 7.84 (dd, J = 8.2,.3 Hz, 2H), 7.69 (d, J = 2.7 Hz, H), 7.58 7.54 (m, H), 7.50 7.44 (m, 3H), 7.35 7.33 (m, 2H). C NMR (25 MHz, CDCl 3 -d ): δ 207.8, 40.7, 6.3, 3.5,.3, 28.8, 28.3, 26.40, 24.0, 22.8, 22.6,.3. GC MS (EI, 70 ev) m/z = 22 [M + ]. 3-Propionylpyrrole 2 N H H NMR (500 MHz, CDCl 3 -d ): δ 9.62 (s, H), 7.04 7.02 (m, H), 6.93 6.9 (m, H), 6.29 6.26 (m, H), 2.84 2.79 (q, 2H),.24.20 (t, 3H). C NMR (25 MHz, CDCl 3 -d ): δ 9.6,.7, 24.3, 5.8, 0.5, 3., 9.0. GC MS (EI, 70 ev) m/z = 23 [M + ]. 3-Benzoylpyrrole N H S9
H NMR (500 MHz, CDCl 3 -d ): δ 9.58 (s, H), 7.85 7.83 (m, 2H), 7.52 7.49 (m, H), 7.44 7.4 (m, 2H), 7.09 7.08 (m, H), 6.84 6.83 (m,h), 6.30 6.28 (m, H). C NMR (25 MHz, CDCl 3 -d ): δ 84.7, 8.3,.8, 28.9, 28.3, 25.0, 9.3, 7.4,.0. GC MS (EI, 70 ev) m/z = 7 [M + ]. 3-Propionylbenzofurane 4 H NMR (500 MHz, CDCl 3 -d ): δ 8.25 (s, 2H), 7.54 7.5 (m, H), 7.38 7.36 (m, 2H), 2.94 2.88 (q, 2H),.28.25 (t, 3H). C NMR (25 MHz, CDCl 3 -d ): δ 96.36, 55.63, 50.53, 25.55, 24.49, 24.36, 22.90, 2.99,.46, 33.7, 8.23. GC MS (EI, 70 ev) m/z = 74 [M + ]. 3-Propionyl-5-bromoindole 5 Br N H H NMR (300 MHz, DMS-d 6 ): δ 2.06 (br s, H), 8.35 (s, H), 8.3 (d, J = 2.0 Hz, H), 7.42 (d, J = 8.6 Hz, H), 7.3 (dd, J = 8.6, 2.0 Hz, H), 2.85 (q, J = 7.4 Hz, 2H),.09 (t, J = 7.4 Hz, 3H). C NMR (75 MHz, DMS-d 6 ): δ 96.4, 5.8, 5.2, 27.6, 25.7, 23.9, 5.9, 4.8, 4.6, 32.3, 9.4. GC MS (EI, 70 ev) m/z = 253 [M + ]. 3-Propionyl-4-bromoindole S0
Br N H Reddish brown solid, mp. 2 C. H NMR (500 MHz, CDCl 3 -d ): δ 9.59 (br s, H), 7.40 (dt, J = 8.3, 0.8 Hz, H), 7.33 (dd, J = 7.5, 0.7 Hz, H), 7.24 (dd, J = 2.3, 0.9 Hz, H), 7.9 (dd, J = 8.2, 7.6 Hz, H), 3.04 (q, J = 7.4 Hz, 2H),.30 (t, J = 7.4 Hz, 3H). C NMR (25 MHz, CDCl 3 -d ): δ 94., 7.4, 5.0, 28.5, 26.8, 23.8, 6.8,.5, 08.9, 3.6, 8.6. GC MS (EI, 70 ev) m/z = 25 [M + ]. HR-ESI-MS: m/z calcd for ([M+Na] + ) 273.9838, found 273.984.. 3-Propionyl-5-chloroindole 6 Cl N H H NMR (500 MHz, CDCl 3 -d ): δ 8.57 (br s, H), 8.4 (d, J =.9 Hz, H), 7.88 (d, J = 2.4 Hz, H), 7.33 (d, J = 8.6 Hz, H), 7.24 (dd, J = 8.7, 2.4 Hz, H), 2.90 (q, J = 7.4 Hz, 2H),.26 (t, J = 7.4 Hz, 3H). C NMR (25 MHz, CDCl 3 -d ): δ 96.5, 8.7, 7.3, 4.6,.3, 24., 22.2, 7.7, 2.2, 33.0, 29.7, 8.8. GC MS (EI, 70 ev) m/z = 207 [M + ]. 3-Propionyl-5-fluoroindole 7 F N H S
H NMR (500 MHz, CDCl 3 -d ): δ 8.64 (s, H), 8.08 (dd, J = 9.7, 2.5 Hz, H), 7.90 (d, J = 2.5 Hz, H), 7.33 (dd, J = 8.8, 4.3 Hz, H), 7.03 (td, J = 8.9, 2.5 Hz, H), 2.90 (q, J = 7.4 Hz, 2H),.26 (t, J = 7.4 Hz, 3H). C NMR (25 MHz, CDCl 3 -d ): δ 96.6, 59.6 (d, J = 239.4 Hz), 2.3 (d, J = 20.8), 26.3 (d, J =. Hz), 8., 2.2 (d, J = 25.0 Hz), 07.9 (d, J = 25.0 Hz), 32.9, 8.8. GC MS (EI, 70 ev) m/z = 9 [M + ]. 3-Propionyl-5-methylindole N H Pale yellow solid, mp. 208 209 C H NMR (300 MHz, DMS-d 6 ): δ.75 (br s, H), 8.23 (s, H), 8.04 7.93 (m, H), 7.33 (d, J = 8.3 Hz, H), 7.02 (dd, J = 8.3,.5 Hz, H), 2.84 (q, J = 7.4 Hz, 2H), 2.39 (s, 3H),.0 (t, J = 7.4 Hz, 3H). C NMR (75 MHz, DMS-d 6 ): δ 95.7, 4.9, 3.4, 0.3, 25.7, 24., 2.0, 5.6,.6, 3.8, 2.3, 9.2. GC MS (EI, 70 ev) m/z: 87 [M + ]. HR-ESI-MS: m/z calcd for ([M+Na] + ) 20.0889, found 20.097. 3-Propionyl-5-methoxyindole N H White solid, mp. 82 83 C H NMR (300 MHz, DMS-d 6 ): δ.74 (br s, H), 8.2 (s, H), 7.69 (d, J = 2.5 Hz, H), 7.33 (d, J = 8.8 Hz, H), 6.8 (dd, J = 8.8, 2.6 Hz, H), 3.75 (s, 3H), 2.82 (q, J = 7.4 Hz, 2H),.09 (t, J = 7.4 Hz, 3H). S2
3 C NMR (75 MHz, DMS-d 6 ): δ 95.7, 55.3, 3.6,.4, 26., 5.8, 2.7, 2. 03.0, 55.2, 3.7, 9.. GC MS (EI, 70 ev) m/z: 203 [M + ]. HR-ESI-MS m/z calcd for ([M+Na] + ) 226.0839, found 226.0856. Section 5. References. Abbott, A. P.; Capper, G.; Davies, D. L.; Munro, H. L.; Rasheed, R. K.; Tambyrajah, V., Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains. Chem. Commun. 200, 200-20. 2. Tran, P. H.; Hansen, P. E.; Hoang, H. M.; Chau, D.-K. N.; Le, T. N., Indium triflate in - isobutyl-3-methylimidazolium dihydrogen phosphate: an efficient and green catalytic system for Friedel Crafts acylation. Tetrahedron Lett. 205, 56, 287-292. 3. Tran, P. H.; Tran, H. N.; Hansen, P. E.; Do, M. H. N.; Le, T. N., A simple, effective, green method for the regioselective 3-acylation of unprotected indoles. Molecules 205, 20, 9605-969. 4. Tran, P. H.; Duus, F.; Le, T. N., Friedel Crafts acylation using bismuth triflate in [BMI][PF 6 ]. Tetrahedron Lett. 202, 53, 222-224. 5. Hachiya, l.; Moriwaki, M.; Kobayashi, S., Catalytic Friedel-Crafts acylation reactions using hafnium triflate as a catalyst in lithium perchlorate-nitromethane Tetrahedron Lett. 995, 36, 409-42. 6. Tran, P. H.; Hansen, P. E.; Pham, T. T.; Huynh, V. T.; Huynh, V. H.; Thi Tran, T. D.; Huynh, T. V.; Le, T. N., Microwave-Assisted Facile and Rapid Friedel Crafts Benzoylation of Arenes Catalyzed by Bismuth Trifluoromethanesulfonate. Synth. Commun. 204, 44, 292-2929. 7. Roux, C. L.; Dubac, J., Bismuth(III) chloride and triflate: Novel catalysts for acylation and sulfonylation reactions. Synlett 2002, 8-200. 8. Stalick, W. M.; Wynne, J. H.; Lloyd, C. T.; Jensen, S. D.; Boson, S., 3-Acylindoles via a one-pot, regioselective Friedel-Crafts reaction. Synthesis 2004, 2277-2282. 9. kauchi, T.; Itonaga, M.; Minami, T.; wa, T.; Kitoh, K.; Yoshino, H., A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminum chloride. rg. Lett. 2000, 2, 485-487. 0. Das, T.; Chakraborty, A.; Sarkar, A., Palladium catalyzed addition of arylboronic acid or indole to nitriles: synthesis of aryl ketones. Tetrahedron Lett. 204, 55, 798-7202.. Lai, Q. Y.; Liao, R. S.; Wu, S. Y.; Zhang, J. X.; Duan, X. H., A novel microwave-irradiated solvent-free 3-acylation of indoles on alumina. New J. Chem. 20, 37, 4069. 2. Garrido, D. A.; Buldain, G.; jea, M. I.; Frydman, B., Synthesis of 2-alkylputrescines from 3- alkylpyrroles. J. rg. Chem. 988, 53, 403-407.. Voigt, M.; Rohde, N.; L, M.; Hallensleben, The influence of water on the electrochemical polymerization of 3-acylpyrroles. Synthetic Metals 993, 55, 489-494. 4. Brewer, J. D.; Elix, J. A. Annelated furans. XV. The autoxidation of tetrahydrodibenzofurans, Aust. J. Chem. 975, 28, 059-08. S
5. Preobrazhenskaya, M. N.; rlova, L. M.; Suvorov, N. N., Bromination of 3-acylindoles. Zh. Vses. Khim. bshchest. 968,, 236-237. 6. Lamattina, J. L.; McCarthy, P. A.; Reiter, L. A. Preparation of 2-guanidino-4-arylthiazoles for treatment of peptic ulcers. EP259085A, 988 7. Jiang, T.-S.; Wang, G.-W., Synthesis of 3-acylindoles by palladium-catalyzed acylation of free (N-H) indoles with nitriles. rg. Lett. 20, 5, 788-79. S4
Section 6. NMR spectra H and C NMR of 4-methoxypropiophenone S5
H and C NMR of propionylindole S6
S7
H and C NMR of 4-methoxyacetophenone S8
H and C NMR of 4-methoxybutyrophenone S9
H and C NMR of 4-methoxybenzophenone S20
H and C NMR of 3,4-dimethoxybenzophenone S2
H and C NMR of 3,4-dimethoxypropiophenone S22
H and C NMR of 2,4-dimethoxybenzophenone S23
H and C NMR of 2,5-dimethoxybenzophenone S24
H and C NMR of 2,4,5-trimethoxybenzophenone S25
H and C NMR of 2,4,6-trimethylbenzophenone S26
H and C NMR of 2,4,6-trimethylpropiophenone S27
H and C NMR of 2,4-dimethylbenzophenone S28
H and C NMR of 2, 5-dimethylpropiophenone S29
H and C NMR of 2,5-dimethylbenzophenone S30
H and C NMR of 4-isopropylbenzophenone S3
H and C NMR of 4-methylthiobenzophenone S32
H and C NMR of 3-acetylindole N H N H S33
H and C NMR of 3-butyrylindole S34
H and C NMR of 3-isobutyrylindole S35
H and C NMR of 3-pivaloylindole S36
H and C NMR of 3-benzoylindole S37
H and C NMR of 3-propionylpyrrole S38
H and C NMR of 3-benzoylpyrrole S39
H and C NMR of 3-propionylbenzofurane S40
H and C NMR of 3-propionyl-5-bromoindole S4
H and C NMR of 3-propionyl-4-bromoindole S42
H and C NMR of 3-propionyl-5-chloroindole S43
H and C NMR of 3-propionyl-5-fluoroindole S44
H and C NMR of 3-propionyl-5-methylindole S45
H and C NMR of 3-propionyl-5-methoxylindole S46