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d 196.9, 156.4, 145.6, 138.8, 138.1, 137.2, 136.6, 133.3, 132.7, NMR (100 MHz, CDCl3) d 198.3, 155.2, 145.9, 135.3, 133.1, 132.9,
132.3, 130.8, 130.6, 129.4, 128.7, 127.6, 126.0, 122.7, 121.2, 130.9, 129.0, 128.1, 122.4, 120.5, 120.5, 25.3, 22.6, 14.2; HRMS
21.34, 21.32; HRMS (ESI) Calcd for C25H22ONa [M + Na]: m/z (ESI) Calcd for C17H15O [M + H]: m/z 235.1124. Found: 235.1100.
361.1568. Found: 361.1567.
2,3-Bis(3,5-dimethoxyphenyl)-1-indenone (3ah). A mixture of
benzaldehyde 1a (0.053 g, 0.5 mmol) and 1,2-bis(3,5-
Conflicts of interest
dimethoxyphenyl)ethyne (0.178 g, 0.6 mmol) was stirred at There are no conicts to declare.
130 ꢀC for 6 h. The residue was puried by ash chromatog-
raphy over silica gel (hexane/ethyl acetate, 95 : 5) to afford the
Acknowledgements
desired product 3ah as a red solid. IR (KBr, cmꢁ1) 2913, 1709,
1594, 1452; 1H NMR (400 MHz, CDCl3) d 7.56 (d, J ¼ 5.6 Hz, 1H), We thank UGC-DSK (New Delhi) for the Dr D. S. Kothari
7.37 (dt, J ¼ 0.9, 5.9 Hz, 1H), 7.28 (dt, J ¼ 0.6, 5.8 Hz, 1H), 7.17 (d, fellowship. JK also thank to Prof. K. C. Kumaraswamy for his
J ¼ 5.8 Hz, 1H), 6.52 (d, J ¼ 1.8 Hz, 2H), 6.49 (t, J ¼ 1.8 Hz, 1H), expert suggestions. RK acknowledges to the DST for the nan-
6.47 (d, J ¼ 1.8 Hz, 2H), 6.36 (t, J ¼ 1.8 Hz, 1H), 3.71 (s, 6H), 3.65 cial support under the early career research award scheme
(s, 6H); 13C NMR (100 MHz, CDCl3) d 196.2, 161.0, 160.2, 155.6, (project no. ECR/2018/000637). We also thank Director CSIR-
145.0, 134.5, 133.5, 132.4, 132.2, 130.6, 129.0, 122.9, 121.4, IICT for the support (IICT/Pubs/2019/352).
107.8, 106.3, 101.4, 100.8, 55.4, 55.2; HRMS (ESI) Calcd for
C
25H22O5Na [M + Na]: m/z 425.1365. Found: 425.1362.
2,3-Bis(3,4-dimethoxyphenyl)-1-indenone (3ai). A mixture of
Notes and references
benzaldehyde 1a (0.053 g, 0.5 mmol) and 1,2-bis(3,4-
dimethoxyphenyl)ethyne (0.178 g, 0.6 mmol) was stirred at
130 ꢀC for 6 h. The residue was puried by ash chromatog-
raphy over silica gel (hexane/ethyl acetate, 95 : 5) to afford the
desired product 3ai as a red solid. IR (KBr, cmꢁ1) 2915, 1693,
1632, 1452; 1H NMR (400 MHz, CDCl3) d 7.57 (d, J ¼ 5.4 Hz, 1H),
7.39 (dt, J ¼ 6.0, 0.8 Hz, 1H), 7.29 (dt, J ¼ 5.9, 0.6 Hz, 1H), 7.21 (d,
J ¼ 5.8 Hz, 1H), 7.08 (dd, J ¼ 6.6, and 1.5 Hz, 1H), 6.95 (d, J ¼
6.7 Hz, 2H), 6.88 (dd, J ¼ 9.9 Hz and J ¼ 1.5 Hz, 2H), 6.81 (d, J ¼
6.7 Hz, 1H), 3.95 (s, 3H), 3.88 (s, 3H), 3.73 (s, 3H), 3.70 (s, 3H);
13C NMR (100 MHz, CDCl3) d 196.8, 153.9, 149.9, 149.1, 148.7,
148.4, 145.3, 133.3, 131.3, 131.0, 128.7, 125.4, 123.6, 123.0,
122.7, 121.6, 120.9, 113.1, 111.9, 111.3, 110.9, 55.9, 55.8, 55.6;
HRMS (ESI) Calcd for C25H22O5Na [M + Na]: m/z 425.1365.
Found: 425.1363.
2,3-Bis(3,4-dimethoxymethylenephenyl)-1-indenone (3aj). A
mixture of benzaldehyde 1a (0.053 g, 0.5 mmol) and 1,2-bis(3,4-
dimethoxymethylenephenyl)ethyne (0.159 g, 0.6 mmol) was
stirred at 130 ꢀC for 6 h. The residue was puried by ash
chromatography over silica gel (hexane/ethyl acetate, 99 : 1) to
afford the desired product as a red solid. IR (KBr, cmꢁ1) 2914,
1699, 1630, 1499; 1H NMR (400 MHz, CDCl3) d 7.56 (d, J ¼
7.0 Hz, 1H), 7.38 (dt, J ¼ 7.5, 1.1 Hz, 1H), 7.28 (dt, J ¼ 7.7, 0.9 Hz,
1H), 7.17 (d, J ¼ 7.2 Hz, 1H), 6.95 (dd, J ꢃ8.1, J ¼ 1.7 Hz, 1H),
6.86 (d, J ¼ 8.0 Hz, 1H), 6.84 (dd, J ꢃ8.4 Hz and J ¼ 1.6 Hz, 2H),
6.79–6.77 (m, 2H), 6.05 (s, 2H), 5.96 (s, 2H);13C NMR (100 MHz,
CDCl3) d 196.5, 154.1, 148.5, 148.0, 147.4, 147.3, 145.2, 133.4,
131.6, 130.8, 128.8, 126.4, 124.6, 124.2, 122.9, 121.1, 110.2,
108.9, 108.8, 108.4, 101.4, 101.0; HRMS (ESI) Calcd for C23H15O5
[M + H]: m/z 371.0919. Found: 371.0917.
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2-Propyl,3-phenyl-1-indenone (3ak). A mixture of benzalde-
hyde 1a (0.053 g, 0.5 mmol) and 1-phenylbutyne (0.6 mmol) was
stirred at 130 ꢀC for 6 h. The residue was puried by ash
chromatography over silica gel (hexane/ethyl acetate, 99 : 1) to
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afford the desired product 3ak as a red solid. IR (KBr, cmꢁ1
)
1
2914, 1703, 1615, 1447; H NMR (400 MHz, CDCl3) d 7.59–7.41
v(m, 6H), 7.39–7.18 (m, 2H), 7.12 (d, J ¼ 7.0 Hz, 1H), 2.72–2.31
(m, 2H), 1.56–1.48 (m, 2H), 0.90 (t, J ¼ 7.0 and 2.1 Hz, 3H); 13
C
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RSC Adv., 2019, 9, 31162–31168 | 31167