Abstract
The iodine-catalyzed reaction of 2-(2-aminophenyl)quinazolin-4(3H)-ones and benzaldehydes was treated in ionic liquids, giving a series of 6-aryl-5H-quinazolino[4,3-b]quinazolin-8(6H)-one derivatives in high yields. This novel procedure has the advantages of high yields, being metal-free and having a mild reaction condition.
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J. Cai, M. Sun, X. Wu, J. Chen, P. Wang, X. Zong, M. Ji, Design and synthesis of novel 4-benzothiazole amino quinazolines Dasatinib derivatives as potential anti-tumor agents. Eur. J. Med. Chem. 63, 702 (2013)
S. Mowafy, N.A. Farag, K.A.M. Abouzid, Design, synthesis and in vitro anti-proliferative activity of 4,6-quinazolinediamines as potent EGFR-TK inhibitors. Eur. J. Med. Chem. 61, 132 (2013)
M.J. Hour, S.C. Tsai, H.C. Wu, M.W. Lin, J.G. Chung, J.B. Wu, J.H. Chiang, M. Tsuzuki, J.S. Yang, Antitumor effects of the novel quinazolinone MJ-33: inhibition of metastasis through the MAPK, AKT, NF-κB and AP-1 signaling pathways in DU145 human prostate cancer cells. Int. J. Oncol. 41, 1513 (2012)
A.I. Markosyan, S.V. Dilanyan, F.G. Arsenyan, R.S. Sukasyan, I.S. Sarkisyan, B.T. Garibdzhanyan, Synthesis, antitumor, and anti-monoamine oxidase properties of 2,4,4-trisubstituted triazolobenzo[h]quinazolines. Pharm. Chem. J. 44, 111 (2014)
S. Mahboobi, A. Sellmer, M. Winkler, E. Eichhorn, H. Pongratz, T. Ciossek, T. Baer, T. Maier, T. Beckers, Novel chimeric histone deacetylase inhibitors: a series of lapatinib hybrides as potent inhibitors of epidermal growth factor receptor (EGFR), human epidermal growth factor receptor 2 (HER2), and histone deacetylase activity. J. Med. Chem. 53, 8546 (2010)
P. Chaitanya, G.D. Reddy, G. Varun, L.M. Srikanth, V.V.S.R. Prasad, A. Ravindernath, Design and synthesis of quinazolinone derivatives as anti-inflammatory agents: pharmacophore modeling and 3D QSAR studies. Med. Chem. 10, 711 (2014)
Y.N. Mabkhot, M.S. Al-Har, A. Barakat, F.D. Aldawsari, A. Aldalbahi, Z. Ul-Haq, Synthesis, anti-microbial and molecular docking studies of quinazolin-4(3H)-one derivatives. Molecules 19, 8725 (2014)
H. Xiao, P. Li, D. Hu, B.A. Song, Synthesis and anti-TMV activity of novel β-amino acid ester derivatives containing quinazoline and benzothiazole moieties. Bioorg. Med. Chem. Lett. 24, 3452 (2014)
H.K. Maurya, R. Verma, S. Alam, S. Pandey, V. Pathak, S. Sharma, K.K. Srivastava, A.S. Negi, A. Gupta, Studies on substituted benzo[h]quinazolines, benzo[g]indazoles, pyrazoles, 2,6-diarylpyridines as anti-tubercular agents. Bioorg. Med. Chem. Lett. 23, 5844 (2013)
M.Y. Ebeid, M. Abdel-Samei Amin, S. El-Sayed Barakat, M.K. Ibrahim, A.-G.A. El-Helby, H.M. Sakr, Synthesis and pharmacological evaluation of some new quinazolino[1,2-c]quinazolinone and 1,2,4-triazino[4,3-c]quinazoline analogs. Saudi Pharm. J. 6, 127 (1998)
A. Kamal, P.B. Sattur, Synthesis of 5-aryl-12H-quinazolino[3,2-a]quinazolin-12-ones as antiinflammatory agents. Arch. Pharm. 316, 702 (1983)
K. Ozaki, Y. Yamada, T. Oine, Studies on 4(1H)-quinazolinones. 2. Synthesis of 6a,7-dihydro-5H-quinazolino[1,2-a]quinazoline-5,8(6H)-diones. J. Org. Chem. 46, 1571 (1981)
J. Fu, M. Liu, J. Chen, J. Ding, Y. Hu, H. Wu, Copper-catalyzed sequential arylation and intramolecular annulation of 2-(2-bromophenyl)-2,3-dihydroquinazolin-4(1H)-ones with amidines. RSC Adv. 3, 24001 (2013)
S. Venkateswarlu, M. Satyanarayana, P. Ravikiran, V. Siddaiah, Reaction of imidoformates with anthranilates: facile, one-pot, three-component synthesis of 8H-quinazolino[4,3-b]quinazolin-8-ones. J. Heterocycl. Chem. 50, 1089 (2013)
S. Venkateswarlu, M. Satyanarayana, V. Siddaiah, Facile one-pot synthesis of 8H-quinazolino[4,3-b]quinazolin-8-ones. Synth. Commun. 43, 85 (2013)
G. Qiu, Y. He, J. Wu, Preparation of quinazolino[3,2-a]quinazolines via a palladium-catalyzed three-component reaction of carbodiimide, isocyanide, and amine. Chem. Commun. 48, 3836 (2012)
A.D. Roy, A. Subramanian, R. Roy, Auto-redox reaction: tin(II) chloride-mediated one-step reductive cyclization leading to the synthesis of novel bi-heterocyclic 5,6-dihydro-quinazolino[4,3-b]quinazolin-8-ones with three-point diversity. J. Org. Chem. 71, 382 (2006)
F. Alexandre, A. Berecibar, R. Wrigglesworth, T. Besson, Novel series of 8H-quinazolino[4,3-b]quinazolin-8-ones via two Niementowski condensations. Tetrahedron 59, 1413 (2003)
P. Hanumanthu, C.V. Ratnam, Studies in the formation of heterocyclic rings containing nitrogen: Part XXVII. Condensation of 2,3-dihydro-2-(o-aminophenyl)-4(1H)-quinazolinone with Schiff bases and heteroaromatization of the resulting products. Indian J. Chem. Sect. B 17B, 349 (1979)
J. Azizian, A.A. Mohammadi, A.R. Karimi, M.R. Mohammadizadeh, Synthesis of some new 6-substituted quinazolino[4,3-b]quinazolin-8-ones under solvent-free conditions, J. Chem. Res. 435(2004)
S. Venkateswarlu, M. Satyanarayana, G.N. Murthy, V. Siddaiah, Cyclisation of 2-(2-aminophenyl)quinazolin-4(3H)-one reexamined: formation of isomeric angular fused quinazolinoquinazolinones and their spectroscopic identification. Tetrahedron Lett. 53, 2643 (2012)
X.S. Wang, M.Y. Yin, W. Wang, S.J. Tu, A stereoselective Povarov reaction leading to exo-tetrahydroindolo[3,2-c]quinoline derivatives catalyzed by iodine. Eur. J. Org. Chem. 4811(2012)
L. Lu, M.M. Zhang, H. Jiang, X.S. Wang, Structurally diversified products from the reactions of 2-aminobenzamides with 1,3-cyclohexanediones catalyzed by iodine. Tetrahedron Lett. 54, 757 (2013)
D.S. Chen, Y.L. Li, Y. Liu, X.S. Wang, Synthesis of bis-benzoquinoline derivatives catalyzed by iodine via ring-opening of furan. Tetrahedron 69, 7045 (2013)
X.S. Wang, J. Sheng, L. Lu, K. Yang, Y.L. Li, Combinatorial synthesis of 3-arylideneaminoquinazolin-4(1H)-one derivatives catalyzed by iodine in ionic liquids. ACS Comb. Sci. 13, 196 (2011)
R.K. Rai, A. Mahata, S. Mukhopadhyay, S. Gupta, P.Z. Li, K.T. Nguyen, Yl Zhao, B. Pathak, S.K. Singh, Room-temperature chemoselective reduction of nitro groups using non-noble metal nanocatalysts in water. Inorg. Chem. 53, 2904 (2014)
Acknowledgments
We are grateful to the National Natural Science foundation of China (20802061), the Major Natural Science Foundation of Jiangsu Province (14KJA150004) and a project funded by the Priority Academic Program Development of Jiangsu Higher Education for financial support.
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Ma, YG., Zhang, Y., Feng, BB. et al. Synthesis of 6-aryl-5H-quinazolino[4,3-b]quinazolin-8(6H)-one derivatives in ionic liquids catalyzed by iodine. Res Chem Intermed 42, 1045–1055 (2016). https://doi.org/10.1007/s11164-015-2072-8
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DOI: https://doi.org/10.1007/s11164-015-2072-8