AN EFFICIENT GREEN APPROACH TO ALDOL AND CROSS-ALDOL CONDENSATIONS
1077
10. Hsieh, C.-T., Hsieh, T.-J., El-Shazly, M., Chuang, D.-W.,
Tsai, Y.-H., Yen, C.-T., Wu, S.-F., Wu, Y.-C., and
Chang, F.-R., Bioorg. Med. Chem. Lett., 2012, vol. 22,
no. 12, p. 3912. doi 10.1016/j.bmcl.2012.04.108
11. Kumar, H., Devaraji, V., Joshi, R., Jadhao, M., Ahirkar, P.,
Prasath, R., Bhavana, P., and Ghosh, S. K., RSC Adv.,
2015, vol. 5, no. 80, p. 65496. doi 10.1039/C5RA08778C
12. Mahapatra, D.K., Asati, V., and Bharti, S.K., Eur. J.
Med. Chem., 2015, vol. 92, p. 839. doi 10.1016/
j.ejmech.2015.01.051
Harom), 7.77 d (1H, J = 15.7 Hz, CHvinyl), 8.03 d (2H,
J = 7.1 Hz, Harom).
1-Phenyl-3-(p-tolyl)prop-2-en-1-one (3s). Yield
1
91% (17 min), mp 91–93°C (179°C [40]). H NMR
spectrum, δ, ppm: 2.43 s (3H, CH3), 7.27 d (2H, J =
8.1 Hz, Harom), 7.47 d (1H, J = 15.6 Hz, CHvinyl), 7.49–
7.67 m (6H, Harom), 7.83 d (1H, J = 15.6 Hz, CHvinyl),
8.04 d (2H, J = 7.6 Hz, Harom).
3-(2-Nitrophenyl)-1-phenylprop-2-en-1-one (3t).
13. Mahapatra, D.K. and Bharti, S.K., Life Sci., 2016,
vol. 148, p. 154. doi 10.1016/j.lfs.2016.02.048
1
Yield 92% (19 min), mp 120–122°C (179°C [40]). H
NMR spectrum, δ, ppm: 7.35 d (1H, J = 15.7 Hz,
CHvinyl), 7.50–7.85 m (6H, Harom), 7.96–8.12 m (3H,
Harom), 8.19 d (1H, J = 15.7 Hz, CHvinyl).
14. Roussaki, M., Hall, B., Lima, S.C., da Silva, A.C.,
Wilkinson, S., and Detsi, A., Bioorg. Med. Chem. Lett.,
2013, vol. 23, no. 23, p. 6436. doi 10.1016/
j.bmcl.2013.09.047
CONCLUSIONS
15. Thillainayagam, M., Pandian, L., Murugan, K.K.,
Vijayaparthasarathi, V., Sundaramoorthy, S., Anbarasu, A.,
and Ramaiah, S., J. Biomol. Struct. Dyn., 2015, vol. 33,
no. 5, p. 961. doi 10.1080/07391102.2014.920277
16. Ahmed, M.R., Sastry, V.G., Bano, N., Ravichandra, S.,
and Raghavendra, M., Rasayan J. Chem., 2011, vol. 4,
no. 2, p. 289.
17. Luo, Y., Song, R., Li, Y., Zhang, S., Liu, Z.-J., Fu, J.,
and Zhu, H.-L., Bioorg. Med. Chem. Lett., 2012,
vol. 22, no. 9, p. 3039. doi 10.1016/j.bmcl.2012.03.080
18. Annapurna, A., Mudagal, M.P., Ansari, A., and Rao, A.S.,
Exp. Clin. Cardiol., 2012, vol. 17, no. 3, p. 110.
19. Mahapatra, D.K., Bharti, S.K., and Asati, V., Eur. J.
Med. Chem., 2015, vol. 98, p. 69. doi 10.1016/
j.ejmech.2015.05.004
NMSDSA efficiently catalyzed the selective aldol
and cross-aldol condensations of ketones with aromatic
aldehydes upon refluxing in water. The fast process
gave high yields, the work-up was easy and only one
product was formed in each case. The catalyst could be
easily recycled and reused for three times with slight
reduction in activity.
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