Amino Acid Catalyzed Synthesis of 2,3-Dihydroquinazolin-4(1H)-One Derivatives
Letters in Organic Chemistry, 2018, Vol. 15, No. 4 249
[7]
Gupta, R.C.; Nath, R.; Shanker, K.; Bhargava, K.P.; Kishore, K. J.
Indian Chem. Soc., 1979, 56, 219-220.
3.2.4. 2-(Pyridine-2-yl)-2,3-dihydroquinazolin-4-(1H)-one,
(Entry 10, Table 3)
Yield: 75%. mp 185ºC. FT-IR (ν, cm-1): 3423 (NH
amine), 1671 (C=O), 1588 (C=C), 1448 (CHben).
1H NMR (DMSO- d6, 400 MHz) δ 8.56 (d, 1H), 8.40 (d,
1H), 7.83 (t, 1H), 7.62 (m, 1H), 7.51 (d, 1H), 7.34 (dd, 1H),
7.24 (m, 2H), 6.76 (d, 1H), 6.66 (t, 1H), 5.72 (t, 1H); 13C
NMR (DMSO- d6, 100 MHz) δ 163.82, 160.72, 149.43,
137.54, 133.79, 127.71, 123.92, 120.97, 117.49, 115.11,
114.89, 67.71;
[8]
Hamel, E.; Lin, C.M.; Plowman, J.; Wang, H.-K.; Lee, H.-H.;Pad,
K.D. Biochem. Pharmacol., 1996, 51, 53-59.
[9]
Kumar, A.; Tyagi, M.; Srivastava, V.K. Indian J. Chem. Sect.,
2003, 42, 2142-2145.
Zhaleh, S.; Hazeri, N.; Maghsoodlou, M.T. Res. Chem. Intermed.,
2016, 42(7), 6381.
[10]
[11]
[12]
[13]
[14]
[15]
[16]
Sandip, B.B.; Nagaraju, M.; Sudhakar, M.; Jaideep, B.B.; Ramesh,
M.; Rammohan, R.Y.; Ram A.V. ARKIVOC, 2012, 8, 308-318.
Matthieu, D.; Martin, S.; Thomas, H. New J. Chem., 2013, 37,
3595.
Abdel-Jalil, R.J.; Voelter, W.; Saeed, M. Tet. Lett., 2004, 45, 3475-
3476.
Abdollahi-Alibeik, M.; Shabani, E. Chin. Chem. Lett., 2011, 22,
1163-1166.
3.2.5. 2-(4-Dimethylamino)phenyl-2,3-dihydroquinazolin-
4-(1H)-one, (Entry 11, Table 3)
Yield: 91%. mp 148ºC. FT-IR (ν, cm-1): 3320 (NH), 1652
(C=O), 1612 (C=C), 1439 (CHAro).
1H NMR (DMSO- d6, 400 MHz) δ 8.11 (s, 4H), 7.63 (d,
4H,), 7.28 (m, 1H), 7.13 (s, 1H), 6.94 (s, 3H), 6.73 (m, 15H),
5.65 (s, 3H), 3.39 (s, 3H), 3.03 (d, 2H); 13C NMR (DMSO-
d6, 100 MHz) δ 164.31, 151.15, 148.69, 133.60, 129.09,
128.18, 127.18, 117.41, 114.85, 112.40, 67.12.
Shi, D.; Rong, L.; Wang, J.; Zhuang, Q.; Wang, X.; Hu, H. Tetra-
hedron Lett., 2003, 44, 3199-3201.
Shaabani, A.; Maleki, A.; Mofakham, H. Syn. Comm., 2008, 38,
3751-3759.
[17]
[18]
Karimi-Jaberi, Z.; Zarei, L. Acta.Chim. Slov., 2013, 60, 178-183.
Ghashang, M.; Mansoor, S.S.; Aswin, K. Res. Chem. Intermed.,
2013, 41, 1-14.
[19]
[20]
[21]
[22]
[23]
[24]
Labade, V.B.; Shinde, P.V.; Shingare, M.S. Tetrahedron Lett.,
2013, 54, 5778-5780.
Davoodnia, A.; Allameh, S.; Fakhari, A.R.; Tavakoli-Hoseini, N.
Chin. Chem. Lett., 2010, 21, 550-553.
Chen, J.; Su, W.; Wu, H.; Liu, M.; Jin, C. Green Chem., 2007, 9,
972-975.
Shaterian, H.R.; Aghakhanizadeh, M. Chem. Intermed., 2014, 40,
1655-1668.
Wang, J.; Zong, Y.; Fu, R.; Niu, Y.; Yue, G.; Quan, Z.; Wang, X.;
Pan, Y. Ultrason. Sonochem., 2014, 21, 29-34.
Safari, J.; Gandomi-Ravandi, S.J. Mol. Catal. A: Chem., 2014, 390,
1-6.
CONCLUSION
In conclusion, a simple, green and effective catalytic syn-
thetic method has been described for the synthesis of 2,3-
dihydroquinazolin-4(1H)-ones via the cyclocondensation of
2-aminobenzamide with aromatic aldehydes and ketone in
water. Simplified operational process, easy post-treatment
process and good to excellent yields are the remarkable ad-
vantages of this synthetic strategy.
[25]
[26]
Safari, J.; Gandomi-Ravandi, S.C.R. Chimie., 2013, 16, 1158-1164.
Maleki1, A.; Aghaei, M.; Ghamari, N.; Kamalzare, M. Int. J. Nano-
sci. Nanotechnol., 2016, 12,215-222.
[27]
[28]
[29]
[30]
[31]
[32]
[33]
Abdollahi-Alibeik, M.; Shabani, E. J. Iranian Chem. Soc., 2013,
11, 351-359.
CONSENT FOR PUBLICATION
Parthasaradhi, Y.; Rakhi, C.; Suresh, S.; Tangenda, S.J. Eur. J.
Med. Chem., 2013, 4, 462-466.
Not applicable.
Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C.F. J. Am. Chem. Soc.,
2001, 123, 5260-5267.
Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev.,
2007, 107, 5471-5569.
CONFLICT OF INTEREST
Ibrahem, I.; Zou, W.; Engqvist, M.; Xu, Y.; Córdova, A. Chem.
Eur. J., 2005, 11, 7024-7029.
The authors declare no conflict of interest, financial or
otherwise.
Ramasastry, S.S.V.; Zhang, H.; Tanaka, F.; Barbas,C. F. J. Am.
Chem. Soc., 2007, 129, 288-289.
Kumar, P.; Matta, A; Singh, S.; Parmar, V.S.; Singh, B.K.; Van der
Eycken, J.; Lec, C.; Van der Eycken, E.V. Syn. Comm., 2017, 47,
756-763.
ACKNOWLEDGEMENTS
Financial support from UGC (MRP-5996/15, Comcode:
TNMD043) is gratefully acknowledged.
[34]
[35]
Ramesh, R.; Nagasundaram, N.; Meignanasundar, D.; Vadivel, P.;
Lalitha, A. Res. Chem. Intermed., 2017, 43, 1767-1782.
(a) Majumdar, B.; Mandani, S.; Bhattacharya, T.; Sarma, D.;
Sarma, T.K. J.Org. Chem., 2017, 82, 2097- 2106. (b) Zhang, Z.-H.;
Lü , H.-Y.; Yang, S.-H.; Gao, J.-W. J. Comb. Chem., 2010, 12,
643-646. (c) Murthy, P. V.; Rambabu, D.; RamaKrishna, G.;
Reddy, C. M.; Prasad, K.R.; Rao, M.V.B.; Pal, M. Tetrahedron.
Lett., 2012, 53, 863-867. (d) Rambabu, D.; Kumar, S.K.; Sreenivas,
B.Y.; Sandra, S.; Kandale, A.; Misra, P.; Rao, M.V.; Pal, M.
Tetrahedron Lett., 2013, 54, 495-501. (e) Naidu, P.P.; Raghunadh,
A.; Rao, K.R.; Mekala, R.; Babu, J.M.; Rao, B.R.; Siddaiah, V.;
Pal, M. Syn. Comm., 2014, 44, 1475-1482.
Mekala, R.; Madhubabu, M.V.; Dhanunjaya, G.; Regati, S.;
Chandrasekhar, K.B.; Sarva. J; Syn. Comm., 2017, 47, 121-130.
Mirjalili, F.; Bamoniri, A.; Azad, S. J. Iranian Chem. Soc., 2017,
14, 47-55.
Alinezhad, H.; Soleymani, E.; Zare, M. Res. Chem. Intermed.,
2017, 43, 457-466.
REFERENCES
[1]
Erlanson, D.A.; McDowell, R.S.; O’Brien, T. J. Med.Chem., 2004,
47, 3463-3482.
Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K.; Naka-
nishi, Y.; Hamel, E.; Lee,K.-H. J. Med. Chem., 2000, 43, 4479-
4487.
Obniska, J.; Kaminski, K. ActaPol. Pharm., 2006, 63, 101-108.
Gangwal, N.A.; Kothawade, U.R.; Galande, A.D.; Pharande, D.S.;
Dhake, A.S. Indian J. Heterocycl. Chem., 2001, 10, 291-294.
Kung, P.-P.; Casper, M.D.; Cook, K.L.; Wilson-Lingardo, L.;
Risen, L.M.; Vickers, T.A.; Ranken, R.; Blyn, L.B.; Wyatt, J.R.;
Cook, P.D.; Ecker, D.J. J. Med. Chem., 1999, 42, 4705-4713.
Harlie, A.; Parish, J.; Gilliom, R.D. J. Med. Chem., 1982, 25, 98-
102.
[2]
[3]
[4]
[36]
[37]
[38]
[5]
[6]