J. Soora Haranath, S. K. Balam, S. S. Chereddy, S. P. Sthanikam, S. Sarva, M. Gundluru,
and S. R. Cirandur
Vol 000
(ESI): m/z 326 [M + H]+. Anal. Calcd for C19H19NO4: C, 70.14; H,
5.89; N, 4.31. Found: C, 70.11; H, 5.78; N, 4.24.
(ESI): m/z 388 [M + H]+. Anal. Calcd for C24H21NO4: C, 74.40;
H, 5.46; N, 3.62. Found: C, 74.31; H, 5.36; N, 3.48.
(4-Bromophenyl)(3-methyl-1H-indol-2-yl)methanone (3d). mp
174–176°C; 1H NMR (300 MHz, CDCl3) δ [ppm]: 2.32 (s, 3H),
7.12–7.14 (m, 1H), 7.34–7.37 (m, 1H), 7.39–7.41 (m, 1H), 7.62–
7.68 (m, 5H), 8.91 (brs, 1H); 13C NMR (75 MHz, CDCl3) δ [ppm]:
11.4, 112.7, 119.9, 120.7, 121.6, 127.3, 127.5, 130.0, 131.1, 132.2,
137.4, 138.9, 187.6; IR (KBr, cmÀ1) 3338, 2932, 1623, 1435, 1342,
588; MS (ESI): m/z 314 [M+ H]+. Anal. Calcd for C16H12BrNO: C,
61.17; H, 3.85; N, 4.46. Found: C, 61.09; H, 3.78; N, 4.38.
2-Methyl-1-(3-methyl-1H-indol-2-yl) propan-1-one (3k).
mp
119–121°C; 1H NMR (300 MHz, CDCl3) δ [ppm]: 1.28 (d,
J= 6.7 Hz, 6H), 3.39–3.51 (m, 1H), 7.06–7.11 (m, 1H), 7.27–7.36
(m, 2H), 7.63 (d, J= 8.3 Hz, 1H), 9.13 (brs, 1H), 13C NMR (75MHz,
CDCl3) δ [ppm]: 10.9, 18.8, 37.1, 111.7, 120.0, 121.1, 126.3, 129.1,
131.4, 136.0, 197.6; IR (KBr, cmÀ1) 3323, 2958, 1632, 1423, 1329;
MS (ESI): m/z 202 [M + H]+. Anal. Calcd for C13H15NO: C, 77.58;
H, 7.51; N, 6.96. Found: C, 76.91; H, 7.36; N, 6.45.
(5,6-Dimethoxy-3-methyl-1H-indol-2-yl)(phenyl)methanone
1
(3e).
mp 163–165°C; H NMR (300 MHz, CDCl3) δ [ppm]:
2.19 (s, 3H), 3.91 (s, 6H), 6.78 (s, 1H), 6.90 (s, 1H), 7.44–7.58
(m, 3H), 7.68–7.70 (m, 2H), 8.79 (brs, 1H); 13C NMR (75 MHz,
CDCl3) δ [ppm]: 11.4, 56.0, 56.2, 93.6, 101.0, 121.1, 122.0,
128.3, 128.6, 128.8, 129.4, 131.5, 132.3, 139.8, 145.9, 146.4,
188.1; IR (KBr, cmÀ1) 3319, 2936, 2863, 1621, 1438, 1321,
1160; MS (ESI): m/z 296 [M + H]+. Anal. Calcd for C18H17NO3:
C, 73.20; H, 5.80; N, 4.74. Found: C, 73.12; H, 5.74; N, 4.63.
(5,6-Dimethoxy-3-methyl-1H-indol-2-yl)(p-tolyl)methanone
(3f). mp 141–143°C; 1H NMR (300 MHz, CDCl3) δ [ppm]: 2.12
(s, 3H), 2.43 (s, 3H), 3.92 (s, 6H), 6.75 (s, 1H), 6.91 (s,1H), 7.30–
7.39 (m, 2H), 7.49–7.60 (m, 2H), 8.68 (brs, 1H); 13C NMR
(75 MHz, CDCl3) δ [ppm]: 11.3, 21.3, 56.1, 56.2, 93.6, 101.2,
125.8, 128.2, 129.1, 132.2, 138.2, 139.8, 144.6, 146.0, 166.5,
176.4; IR (KBr, cmÀ1) 3316, 2924, 2862, 1621, 1442, 1321,
1146; MS (ESI): m/z 310 [M+ H]+. Anal. Calcd for C19H19NO3:
C, 73.77; H, 6.19; N, 4.53. Found: C, 73.67; H, 6.08; N, 4.43.
(5,6-dimethoxy-3-methyl-1H-indol-2-yl)(3,4,5-trimethoxyphenyl)
methanone (3g). mp 190–192°C; 1H NMR (300 MHz, CDCl3) δ
[ppm]: 2.29 (s, 3H), 3.87 (s, 6H), 3.89 (s, 3H), 3.91 (s, 6H), 6.79 (s,
1H), 6.91 (s, 1H), 6.99 (s, 2H), 8.83 (brs, 1H); 13C NMR (75MHz,
CDCl3) δ [ppm]: 11.6, 56.0, 56.1, 56.2, 60.9, 93.5, 100.9, 106.3,
120.5, 121.9, 130.6, 132.2, 134.7, 141.1, 145.9, 151.1, 153.0,
187.2; IR (KBr, cmÀ1) 3352, 2931, 1619, 1452, 1318, 1128; MS
(ESI): m/z 386 [M + H]+. Anal. Calcd for C21H23NO6: C, 65.44; H,
6.02; N, 3.63. Found: C, 65.38; H, 5.88; N, 3.52.
Acknowledgments. We thank Professor C. Devendranath Reddy,
Department of Chemistry, Sri Venkateswara University, Tirupati,
for his helpful discussions and University Grants Commission
(UGC), New Delhi, for providing Senior Research Fellowship
to one of the authors Mr. S. H. Jayaprakash and for funding a
research project (F. No.: 42-281/2013 (SR), Dated:12-03-2013).
REFERENCES AND NOTES
[1] Joule, J. A.; Mills, K. Heterocyclic Chemistry, 4th edn;
Blackwell Science: Oxford, 2000.
[2] Deb, M. L.; Bhuyan, P. J Tetrahedron Lett 2007, 48, 2159.
[3] Foye, W. O.; Williams, D. A.; Lemke, T. L. Principles of
Medicinal Chemistry, 4th edn; Lippincott Williams & Wilkins: Baltimore,
MA, 1995, 553.
[4] Scott, L. J.; Perry, C. M. Drugs 2000, 60, 1411.
[5] Acharya, C.; Dey, S.; Jaisankar, P. Tetrahedron Lett 2012, 53, 5548.
[6] Kumar, K. N.; Kaushik, N.; Pankaj, A.; Kumar, N.; Kim, C. H.;
Kumar, V. A.; Choi, E. H. Molecules 2013, 18, 6620.
[7] Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.;
Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson,
P. S. J Med Chem 1988, 31, 2235.
[8] Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem Rev 2003,
103, 893.
[9] Zhang, G. W.; Wang, L.; Nie, J.; Ma, J. A. Adv Synth Catal
2008, 350, 1457.
Phenyl(3-phenyl-1H-indol-2-yl)methanone (3 h).
mp 192–
[10] Renzetti, A.; Dardennes, E.; Fontana, A.; Maria, P. D.; Sapi, J.;
Gerard, S. J Org Chem 2008, 73, 6824.
[11] Zhao, X. D.; Yu, Z. K.; Xu, T. Y.; Wu, P.; Yu, H. F. Org Lett
2007, 9, 5263.
[12] Walsh, T. F.; Toupence, R. B.; Ujjainwalla, F.; Young, J. R.;
Goulet, M. T. Tetrahedron 2001, 57, 5233.
[13] Fischer, E.; Jourdan, F. Ber Dtsch Chem Ges 1883, 16, 2241.
[14] Newman, S. G.; Lautens, M. J Am Chem Soc 2010, 132, 11416.
[15] Bonnamour, J.; Bolm, C. Org Lett 2011, 13, 2012.
[16] Kraus, G. A.; Guo, H. Org Lett 2008, 10, 3061.
[17] Fernandez, A. V.; Varela, J. A.; Saa, C. Synthesis 2012, 44, 3285.
[18] Jana, S.; Clements, M. D.; Sharp, B. K.; Zheng, N. Org Lett
2010, 12, 3736.
[19] Monguchi, Y.; Mori, S.; Aoyagi, S.; Tsutsui, A.; Maegawa, T.;
Sajiki, H. Org Biomol Chem 2010, 8, 3338.
[20] Oh, C. H.; Karmakar, S.; Park, H.; Ahn, Y.; Kim, J. W. J Am
Chem Soc 2010, 132, 1792.
[21] Kappe, C. O. Angew Chem 2004, 43, 6250.
[22] Caddick, S.; Fitzmaurice, R. Tetrahedron 2009, 65, 3325.
[23] Bacsa, B.; Bosze, S.; Kappe, C. O. J Org Chem 2010, 75, 2103.
[24] Duque, J. G.; Pasquali, M.; Schmidt, H. K. J Am Chem Soc
2008, 130, 15340.
[25] Holtze, C.; Antonietti, M.; Tauer, K. Macromolecules 2006,
39, 5720.
[26] Edwards, W. F.; Young, D. D.; Deiters, A. Org Biomol Chem
2009, 7, 2506.
1
194°C; H NMR (300 MHz, CDCl3) δ [ppm]: 7.01–7.07 (m,2H),
7.08–7.21 (m, 4H), 7.21–7.25 (m, 1H), 7.32–7.38 (m,1H), 7.41–7.53
(m, 4H), 7.62–7.70 (m, 2H), 9.29 (brs, 1H); 13C NMR (75MHz,
CDCl3) δ [ppm]: 111.9, 121.1, 122.0, 126.5, 126.7, 127.4, 127.9,
127.9, 128.8, 129.4, 130.1, 130.6, 130.8, 131.6, 132.1, 133.6, 134.2,
134.5, 143.1, 189.5; IR (KBr, cmÀ1) 3321, 2926, 1619, 1338; MS
(ESI): m/z 298 [M + H]+. Anal. Calcd for C21H15NO: C, 84.82; H,
5.08; N, 4.71. Found: C, 84.69; H, 4.87; N, 4.63.
(3-Phenyl-1H-indol-2-yl)(p-tolyl)methanone (3i). mp 188–
190°C; 1H NMR (300 MHz, CDCl3) δ [ppm]: 2.25 (s, 3H), 7.05–
7.15 (m, 1H), 7.27–7.38 (m, 2H), 7.45–7.66 (m, 4H), 7.63–7.81
(m, 2H), 8.90 (brs, 1H); 13C NMR (75 MHz, CDCl3) δ [ppm]:
21.7, 111.8, 120.9, 122.3, 127.1, 127.6, 128.2, 129.1, 129.6,
130.2, 130.8, 131.7, 132.3, 133.9, 134.7, 143.3, 187.1; IR (KBr,
cmÀ1) 3311, 2923, 2892, 1698, 1426, 1332; MS (ESI): m/z 312
[M + H]+. Anal. Calcd for C22H17NO: C, 84.86; H, 5.50; N,
4.50. Found: C, 84.73; H, 5.42; N, 4.37.
(3-Phenyl-1H-indol-2-yl)(3,4,5-trimethoxyphenyl)methanone
(3j). mp 139–141°C; 1H NMR (300MHz, CDCl3) δ [ppm]: 3.58
(s, 6H), 3.75 (s, 3H), 6.73 (s, 2H), 7.10–7.17 (m, 4H), 7.19 (s, 1H),
7.23–7.65 (m, 4H), 9.22 (brs, 1H); 13C NMR (75 MHz, CDCl3) δ
[ppm]: 155.9, 60.7, 107.2, 113.1, 121.3, 123.8, 126.9, 127.3,
128.2, 128.4, 129.8, 130.5, 131.6, 132.2, 133.4, 134.6, 141.7,
152.5, 188.2; IR (KBr, cmÀ1) 3315, 2920, 1622, 1447, 1336; MS
[27] Rahman, K. M.; Thurston, D. E. Chem Commun 2009, 20,
2875.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet