A novel one-pot and rapid synthesis of polyfunctionalized benzo[a]pyrimido[5’,4’:5,6] pyrido[2,3-c]phenazine derivatives under microwave irradiation
A one-pot, environmentally friendly, and efficient protocol for the
synthesis of novel polyfunctionalized
benzo[aaa]pyrimido[5',4':5,6]pyrido[2,3-ccc]phenazine derivatives has been
reported by a one-pot, four-component sequential reaction between
2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamines, benzaldehydes, and
6-amino-1,3-dimethyluracil in the presence of ppp-TSA as a nontoxic,
inexpensive, ecofriendly, and efficacious solid acid catalyst. Two C-C
bonds, two C=N bonds, and one C-N bond, as well as two new rings, were formed in
this reaction. Through this procedure, compounds with substantial biological
and pharmaceutical properties are generated in a single operation. Factors
such as high yields, less reaction time, operational simplicity, and lack of
any dangerous reagents/solvents have made this process a green one.
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- Parsons, P. J.; Penkett, C. S.; Shell, A. J.
Chem. Rev.
1996
,
96
, 195-206.
- Yazdani-Elah-Abadi, A.; Mohebat, R.; Maghsoodlou, M. T.
RSC Adv.
2016
,
6
, 84326-84333.
- Polshettiwar, V.; Varma, R. S.
Acc. Chem. Res.
2008
,
41
, 629-639.
- Satasia, S. P.; Kalaria, P. N.; Raval, D. K.
Org. Biomol. Chem.
2014
,
12
, 1751-1758.
- Blaney, J. M.; Hansch, C.; Silipo, C.; Vittoria, A.
Chem. Rev.
1984
,
84
, 333-407.
- Castle, R.; Phillips, S.; Katritzky, A.; Rees, C.; Boulton, A.; McKillop, A.
Comprehensive Heterocyclic Chemistry,
Vol. 3
; Pergamon Press: Oxford, UK, 1984.
- Gut, J.
Adv. Heterocycl. Chem.
1963
,
1
, 189-251.
- Ribble, W.; Hill, W. E.; Ochsner, U. A.; Jarvis, T. C.; Guiles, J. W.; Janjic, N.; Bullard, J. M.
Antimicrob. Agents
Chemother.
2010
,
54
, 4648-4657.
- Duan, S.; Place, D.; Perfect, H. H.; Ide, N. D.; Maloney, M.; Sutherland, K.; Price Wiglesworth, K. E.; Wang, K.;
Olivier, M.; Kong, F.
Org. Process Res. Dev.
2016
,
20
, 1191-1202.
- VanderWel, S. N.; Harvey, P. J.; McNamara, D. J.; Repine, J. T.; Keller, P. R.; Quin, J.; Booth, R. J.; Elliott, W.
L.; Dobrusin, E. M.; Fry, D. W.
J. Med. Chem.
2005
,
48
, 2371-2387.
- Singh, G.; Singh, G.; Yadav, A. K.; Mishra, A.
Indian J. Chem.
2002
,
41B
, 430-432.
- Quintela, J.; Peinador, C.; Botana, L.; Estévez, M.; Riguera, R.
Bioorgan. Med. Chem.
1997
,
5
, 1543-1553.
- Bazgir, A.; Khanaposhtani, M. M.; Soorki, A. A.
Bioorg. Med. Chem. Lett.
2008
,
18
, 5800-5803.
- El-Gazzar, A. R. B.; Hafez, H. N.
Bioorg. Med. Chem. Lett.
2009
,
19
, 3392-3397.
- Laursen, J. B.; Nielsen, J.
Chem. Rev.
2004
,
104
, 1663-1686.
- Hafez, H.; Hegab, M.; Ahmed-Farag, I.; El-Gazzar, A.
Bioorg. Med. Chem. Lett.
2008
,
18
, 4538-4543.
- Cimmino, A.; Evidente, A.; Mathieu, V.; Andolfi, A.; Lefranc, F.; Kornienko, A.; Kiss, R.
Nat. Prod. Rep.
2012
,
29
, 487-501.
- Ligon, J. M.; Hill, D. S.; Hammer, P. E.; Torkewitz, N. R.; Hofmann, D.; Kempf, H. J.; Pée, K. H. V.
Pest Manag.
Sci.
2000
,
56
, 688-695.
- Makgatho, M. E.; Anderson, R.; O’Sullivan, J. F.; Egan, T. J.; Freese, J. A.; Cornelius, N.; van Rensburg, C. E.
Drug Dev. Res.
2000
,
50
, 195-202.
- Nishanth Kumar, S.; Nisha, G.; Sudaresan, A.; Venugopal, V.; Sree Kumar, M.; Lankalapalli, R. S.; Dileep Kumar,
B.
Med. Mycol.
2014
,
52
, 482-490.
- Wang, J.; Zhi, X.; Yu, X.; Xu, H.
J. Agric. Food. Chem.
2013
,
61
, 6336-6343.
- Mohebat, R.; Yazdani Elah Abadi, A.; Maghsoodlou, M. T.; Mohammadi, M.
Res. Chem. Intermed.
2016
,
42
,
5915-5926.
- Yazdani-Elah-Abadi, A.; Maghsoodlou, M. T.; Mohebat, R.; Heydari; R.
Chin. Chem. Lett.
2017
,
28
, 446-452.
- Mohebat, R.; Yazdani-Elah-Abadi, A.
Chin. Chem. Lett.
2017
,
28
, 1340-1344.
- Mohebat, R.; Yazdani-Elah-Abadi, A.; Maghsoodlou, M. T.; Hazeri, N.
Chin. Chem. Lett.
2017
,
28
, 943-948.
- Ji, S. J.; Ni, S. N.; Yang, F.; Shi, J. W.; Dou, G. L.; Li, X. Y.; Wang, X. S.; Shi, D. Q.
J. Heterocyclic Chem.
2008
,
45
, 693-702.