One-pot three-component synthesis of hydroquinazolinone derivatives using silicotungstic acid under solvent-free conditions

Document Type : Original Article

Authors

Department of New Materials, Institute of Science and High Technology and Environmental Sciences, Graduate University of Advanced Technology, PO Box 76315-117, Kerman, Iran.

Abstract

Abstract
In this research paper, a simple, efficient and green procedure was reported for the one pot preparation of 2,3-dihydroquinazoline-4(1H)-one derivatives using silicotungstic acid as catalyst. Hydroquinazolinone derivatives can obtained from condensation of isatoic anhydride, aromatic aldehydes and ammonium acetate in good yields. The reaction completed at 100 oC within 10-15 min with yields of 88-94%. Shorter reaction times and higher yields were chieved under under solvent-free conditions.

Graphical Abstract

One-pot three-component synthesis of hydroquinazolinone derivatives using silicotungstic acid under solvent-free conditions

Keywords

Main Subjects

References

1) A. Domling, Chem. Rev. 106 (2006) 17.
2) a) J. Zhu, H. Bienayme, Multicomponent reactions.Wiley: Weinheim, (2005). b) S. Balalaie, S. Ahadi,
N.S. Alavijeh, Multicomponent Reactions, Chapter Book, 2017, pp. 83-116. 
3) a) M. Mamaghani, R. Hossein-Nia J. Heterocycl. Chem. 54 (2017) 1700. b) N.O. Mahmoodi, B.
Sharifzadeh, M. Mamaghani, K. Tabatabaeian, S. Shoja, J. Heterocycl. Chem. 53 (2016) 1646.
4) a) M. Shiri, M.A. Zolfigol, H.G. Kruger, Z. Tanbakouchian, Adv. Heterocycl. Chem. 102 (2011) 139. b) P Salehi, M. Dabiri, M.A. Zolfigol, Heterocycles 60 (2003) 2435.
5) D.J. Connolly, D. Cusack, T.P. O’Sullivan, P.J.
Guiry, Tetrahedron 61 (2006) 10153.
6) D.A. Erlanson, R.S. McDowell, T.O. Brien, J. Med. Chem. 47 (2004) 3463.
7) H.A. Parish, R.D. Gilliom, W.P. Purcell, R.K.
Browne, R.F. Spirk, H.D. White, J. Med. Chem. 25 (1982) 98.
8) E. Hamel, C.M. Lin, J. Plowman, H.K. Wang, K.H. Lee, K.D. Paull, Biochem. Pharmacol. 51 (1996) 53.
9) I.K. Kacker, S.H. Zaheer, J. Indian Chem. Soc. 28 (1951) 344.
10) A. Kamal, E.V. Bharathi, J.S. Reddy, M.J. Ramaiah, D. Dastagiri, M.K. Reddy, A. Viswanath, T.L. Reddy, T.B. Shaik, S.N. Pushpavalli, M.P. Bhadra, Eur. J. Med. Chem. 46 (2011) 691.
11) O. Kenichi, Y. Yoshihisa, O. Toyonari, I. Toru, I. Yoshio, J. Med. Chem. 28 (1985) 568.
12) Y. Kurogi, Y. Inoue, K. Tsutsumi, S. Nakamura, K. Nagao, H. Yo-shitsugu, Y. Tsuda, J. Med. Chem. 39 (1996) 1433.
13) H.J. Hess, T.H. Cronin, A. Scriabine, J. Med. Chem. 11 (1968) 130.
14) M.A. Hussain, A.T. Chiu, W.A. Price, P.B. Timmermans, E. Shefter, Pharm. Res. 5 (1988) 242.
15) N.P. Peet, L.E. Baugh, S. Sunder, J.E. Lewis, E.H. Matthews, E.L. Olberding, D.N. Shah, J. Med. Chem. 29 (1986) 2403.
16) H.L. Yale, M. Kalkastein, J. Med. Chem. 10 (1967) 334.
17) D. Shi, L. Rong, J. Wang, Q. Zhuang, X. Wang, H. Hu, Tetrahedron Lett. 44 (2003) 3199.
18) P. Salehi, M. Dabiri, M.A. Zolfigol, M. Baghbanzadeh, Synlett (2005) 1155.
19) M. Dabiri, P. Salehi, M. Baghbanzadeh, M.A. Zolfigol, M. Agheb, S. Heydari, Catal. Commun. 9 (2008) 785.
20) M. Dabiri, P. Salehi, S. Otokesh, M. Baghbanzadeh, G. Kozehgarya, A.A. Mohammadi, Tetrahedron Lett. 46 (2005) 6123.
21) M. Baghbanzadeh, P. Salehi, M. Dabiri, Kozehgarya, G. Synthesis (2006) 344.
22) P. Salehi, M. Dabiri, M. Baghbanzadeh, M. Bahramnejad, Synth. Commun. 36 (2006) 2287.
23) M. Dabiri, P. Salehi, M. Baghbanzadeh, Monatsh. Chem. 138 (2007) 1191.
24) S. Rostamizadeh, A.M. Amani, R. Aryan, H.R Ghaieni, N. Shadjou, Synth.Commun. 38 (2008) 3567.
25) A. Shaabani, A. Rahmati, J.M. Rad, C. R. Chimie. 11 (2008) 759.
26) A. Shaabani, A. Maleki, H. Mofakham, Synth. Commun. 38 (2008) 3751.
27) S. Rostamizadeh, A.M. Amani, G.H. Mahdavinia, H. Sepehrian, S. Ebrahimi, Synthesis 8 (2010) 1356.
28) A. Davoodnia, S. Allameh, A.R Fakhari, N. Tavakoli-Hoseini, Chin. Chem. Lett. 21(2010) 550.
29) Z. Karimi-Jaberi, R. Arjmandi, Monatsh. Chem. 142 (2011) 631.
30) A. Ghorbani-Choghamarani, T. Taghipour, Lett. Org. Chem. 8 (2011) 470.
31) K. Niknam, M.R Mohammadizadeh, S. Mirzaee, Chin. J. Chem. 29 (2011) 1417.
32) K. Niknam, N. Jafarpour, E. Niknam, Chin. Chem. Lett. 22 (2011) 69. 
33) I. Mohammadpoor-Baltork, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, S. Baghersad, A. Mirj C. R. Chimie 14 (2011) 944.
34) I. Yavari, S. Beheshti, J. Iran. Chem. Soc. 8 (2011) 1030. 
35) A. Rostami, A. Tavakoli, Chin. Chem. Lett. 22 (2011) 1317. 
36) M. Abdollahi-Alibeik, E. Shabani, Chinese Chem. Lett. 22 (2011) 1163. 
37) G. Yassaghi, A. Davoodnia, S. Allameh, A. Zare-Bidaki, N. Tavakoli-Hoseini, Bull. Korean Chem. Soc. 33 (2012) 2724.
38) S. Khaksar, S.M. Talesh, C. R. Chimie 15 (2012) 779. 
39) Z. Karimi-Jaberi, L. Zarei, J. Chem. Res. (2012) 194. 
40) M. Ghashang, Orient. J. Chem. 28 (2012) 1213. 
41) J. Safari, S. Gandomi-Ravandi, J. Mol. Catal. A: Chem. 371 (2013) 135. 
42) A. Rostami, B. Tahmasbi, H. Gholami, H. Taymorian Chin. Chem. Lett. 24 (2013) 211. 
43) J. Safari, S. Gandomi-Ravandi, C. R. Chimie 16 (2013) 1158. 
44) J. Safari, S. Gandomi-Ravandi J. Mol. Catal. A: Chem. 1072 (2014) 173. 
45) M. Tajbakhsh, R. Hosseinzadeh, P. Rezaee, M. Tajbakhsh, Chin. J. Catal. 35 (2014) 58. 
46) A. Ghorbani-Choghamarani, M. Norouzi, J. Mol. Catal. A: Chem. 395 (2014) 172. 
47) J. Safari, S. Gandomi-Ravandi, RSC Adv. 4 (2014) 11654. 
48) H. Alinezhad, M. Tajbakhsh, N. Ghobadi, Res. Rev. Materials Sci. Chem. 3 (2014) 123. 
49) M.A. Bodaghi Fard, A. Mobinikhaledi, M. Hamidinasab Synth. React. Inorg, Met. Org. 44 (2014) 567. 
50) A. Gharib, L. Vojdanifard, N. Noroozi Pesyan, B. R. Hashemi Pour Khorasani, M. Jahangir, M. Roshani Bulg. Chem. Commun. 46 (2014) 667. 
51) M.T. Maghsoodlou, N. Khorshidi, M.R. Mousavi, N. Hazeri, S.M. Habibi-Khorassani, Res. Chem. Intermed. 41 (2015) 7497. 
52) M. Mahdavi, K. Pedrood, M. Safavi, M. Saeedi, M. Pordeli, S.K. Ardestani, S. Emami, M. Adib, A. Foroumadi, A. Shafiee, Eur. J. Med. Chem. 95 (2015) 492. 
53) H.R. Memarian, S. Ebrahimi, H. Amiri Rudbari, H. Sabzyan, V.M. Nardo, J. Iran Chem. Soc. 13 (2016) 1395. 
54) F. Tamaddon, M.T. KazemiVarnamkhasti, Synlett 27 (2016) 2510. 
55) A.M Amani Y. Ghasemi, A. Savardashtaki, K. Zomorodian, E. Mirzaei, B. Zare, H. Sepehrian, Bulg. Chem. Commun. 48 (2016) 395. 
56) M.A. Zolfigol, H. Ghaderi, S. Baghery, L. Mohammadi J. Iran Chem. Soc. 14 (2017) 121. 
57) M. Nikoorazm, A. Ghorbani-Choghamarani, M. Khanmoradi, J. Iran Chem. Soc. 14 (2017) 1215. 
58) B.F. Mirjalili, A. Bamoniri, A.S. Azad, J. Iran. Chem. Soc. 14 (2017) 47. 
59) S.Y. Afsar, G. Mohammadi Ziarani, H. Mollabagher, P. Gholamzadeh, A. Badiei, A. Abolhasani Soorki, J. Iran. Chem. Soc. 14 (2017) 577. 
60) N. Noori, M. Nikoorazm, A. Ghorbani- Choghamarani, Cat. Lett. 147 (2017) 204. 
61) M. Esmaeilpour, J. Javidi, S. Zahmatkesh, N. Fahimi, Monatsh. Chem. 148 (2017) 947. 
62) H. Alinezhad, E. Soleymani, M. Zare, Res. Chem. Intermed. 43 (2017) 457. 
63) R. Ghorbani-Vaghei, A. Shahriari, Y. Maghbooli, J. Mahmoudi, Res. Chem. Intermed. 43 (2017) 983. 
64) L. Shiri, M. Kazemi, Res. Chem. Intermed. 43 (2017) 4813. 
65) A. Maleki, T. Kari, M. Aghaei, J. Porous. Mat. 24 (2017) 1481. 
66) N. Azizi, F. Shirdel, Res. Chem. Intermed. 43 (2017) 3873. 
67) Y.S Abbas, K.A.M. El-Bayouki, W.M. Basyouni Synth. Commun. 46 (2016) 993.
 
Iranian Journal of Chemistry
Volume 1, Issue 1 - Serial Number 1
January 2019
Pages 32-38

Files

History

  • Receive Date: 19 May 2018
  • Revise Date: 18 September 2018
  • Accept Date: 24 September 2018

Share

How to cite

Statistics