Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.
C
A. Gorepatil et al.
Letter
Synlett
Williams, M. T., Eds.; Wiley-VCH: Weinheim, 2010, Chap. 1 1.
(c) Selvam, J. J. P.; Suresh, V.; Rajesh, K.; Reddy, S. R.;
Venkateswarlu, Y. Tetrahedron Lett. 2006, 47, 2507. (d) Das, B.;
Krishnaiah, M.; Venkateswarlu, K. Tetrahedron Lett. 2006, 47,
6027. (e) Mantri, K.; Komura, K.; Sugi, Y. Green Chem. 2005, 7,
677. (f) Corma, A.; García, H. Chem. Rev. 2003, 103, 4307.
(g) Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
(h) Shinde, S. S.; Said, M. S.; Surwase, T. B.; Kumar, P. Tetrahe-
dron Lett. 2015, 56, 5916.
2-(4-Chlorophenyl)-2,3-dihydroquinolin-4(1H)-one (Table 2
Entry 2)4a,11,12
Red solid; yield: 249 mg (97%); mp 168–170 °C. IR (KBr): 3343,
3210, 2980, 1666, 1585, 1221, 1150, 750 cm–1 1H NMR (600
.
MHz, CDCl3): δ = 7.83 (dd, J = 7.8, 1.2 Hz, 1 H), 7.38–7.31 (m, 5
H), 6.78 (t, J = 7.2 Hz, 1 H), 6.71 (d, J = 7.8 Hz, 1 H), 4.69 (dd, J =
14.5, 4.2 Hz, 1 H), 4.54 (s, 1 H, NH), 2.79 (dd, J = 17.3, 14.5 Hz, 1
H), 2.71 (dd, J = 17.3, 4.2 Hz, 1 H). 13C NMR (150 MHz, CDCl3):
δ = 193.5, 152.3, 138.4, 136.4, 134.1, 129.2, 127.8, 127.5, 119.2,
118.7, 115.9, 57.8, 46.3. MS (EI): m/z = 257.07 [M+].
(9) (a) Gorepatil, P. B.; Mane, Y. D.; Gorepatil, A. B.; Gaikwad, M. V.;
Ingle, V. S. Res. Chem. Intermed. 2015, 41, 8355. (b) Gorepatil, P.
B.; Mane, Y. D.; Ingle, V. S. Synlett 2013, 24, 2241. (c) Gorepatil,
P. B.; Mane, Y. D.; Ingle, V. S. J. Chem. 2013, DOI:
10.1155/2013/108318.
2-(4-Methoxyphenyl)-2,3-dihydroquinolin-4(1H)-one (Table
2, Entry 10)3e,4a,13
Brown solid; yield: 250 mg (99%); mp 145–147 °C. IR (KBr):
1
3330, 3145, 2978, 2737, 1663, 1585, 1305, 1224, 1132cm–1. H
(10) 2-Aryl-2,3-dihydroquinolin-4(1H)-ones; General Procedure
A mixture of the appropriate 2-aminochalcone (1 mmol), EtOH
(2 mL), H2O (2 mL), and ZrO(NO3)2·nH2O (46 mg, 20 mol%) was
heated with stirring at 50 °C while the progress of the reaction
was monitored by TLC. The reaction was then quenched with
H2O (5 mL), and the mixture was extracted with Et2O (3 × 10
mL). The combined organic extracts were washed with brine (5
mL) then dried (Na2SO4), filtered, and concentrated under
reduced pressure. The crude product was purified by column
chromatography [silica gel, hexane–EtOAc (10:1)].
NMR (300 MHz, CDCl3): δ = 7.85 (dd, J = 7.8, 1.5 Hz, 1 H), 7.37–
7.33 (m, 2 H), 7.31–7.28 (m, 1 H), 6.95–6.86 (m, 2 H), 6.81–6.74
(m, 1 H), 6.67 (d, J = 8.1 Hz, 1 H), 4.69 (dd, J = 13.5, 3.6 Hz, 1 H),
4.33 (s, 1 H, NH), 3.80 (s, 3 H), 2.89–2.70 (m, 2 H). 13C NMR (150
MHz, CDCl3): δ = 193.3, 158.9, 152.1, 135.5, 133.2, 127.9, 127.7,
119.1, 118.4, 116.0, 114.1, 58.0, 55.5, 46.6. MS (EI): m/z = 253.10
[M+].
2-(4-Bromophenyl)-2,3-dihydroquinolin-4(1H)-one (Table 2,
Entry 11)4a,6b,12
Brown solid; yield: 290 mg (96%); mp 167–169 °C. IR (KBr):
2-Phenyl-2,3-dihydroquinolin-4(1H)-one (Table 2, Entry
3324, 3053, 1654, 1492, 1325, 1110, 754 cm–1 1H NMR (300
.
1)5b,6b,11
MHz, CDCl3): δ = 7.85 (dd, J = 7.8, 1.5 Hz, 1 H), 7.53–7.48 (m, 2
H), 7.36–7.30 (m, 3 H), 6.81–6.76 (m, 1 H), 6.70 (d, J = 8.2 Hz, 1
H), 4.71 (dd, J = 17.4, 4.8 Hz, 1 H), 4.44 (s, 1 H, NH), 2.87–2.77
(m, 1 H), 2.77–2.70 (m, 1 H). 13C NMR (75 MHz, CDCl3):
δ = 193.7, 152.3, 141.3, 136.9, 132.3, 128.5, 127.8, 123.4, 119.2,
118.8, 117.1, 58.1, 47.1. MS (EI): m/z = 301.02 [M+].
Off-white solid; yield: 218 mg (98%); mp 153–155 °C. IR (KBr):
3060, 3028, 1638, 1572, 1494, 1358, 1324, 1295, 1157, 1095,
974, 861 cm–1 1H NMR (600 MHz, CDCl3): δ = 7.83 (dd, J = 8.5,
.
1.2 Hz, 1 H), 7.42 (d, J = 7.4 Hz, 2 H), 7.40–7.36 (m, 2 H), 7.35–
7.33 (m, 2 H), 6.76 (t, J = 7.4 Hz, 1 H), 6.68 (d, J = 8.5 Hz, 1 H),
4.70 (dd, J = 13.5, 3.6 Hz, 1 H), 4.65 (s, 1 H, NH), 2.82 (dd, J =
16.3, 14.4 Hz, 1 H), 2.70 (dd, J = 15.6, 3.6 Hz, 1 H). 13C NMR (150
MHz, CDCl3): δ = 192.9, 152.4, 136.1, 128.6, 128.3, 127.4, 126.5,
119.2, 117.2, 116.7, 59.1, 45.7. MS (EI): m/z = 223.10 [M+].
(11) Torii, S.; Okumoto, H.; Xu, L. H.; Sadakane, M.; Shostakovsky, M.
V.; Ponomaryov, A. B.; Kalinin, V. N. Tetrahedron 1993, 49, 6773.
(12) Chandrasekhar, S.; Chatla, S.; Mukhopadhyay, D.; Ganganna, B.;
Vijeender, S.; Srihari, P.; Bhadra, U. Bioorg. Med. Chem. Lett.
2012, 22, 645.
(13) Xiao, Z.-P.; Li, H.-Q.; Shi, L.; Lv, P.-C.; Song, Z.-C.; Zhu, H.-L.
ChemMedChem 2008, 3, 1077.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–C