Citation:
Xin-Xin Qi, Zhen-Zhen Song, Jin-Long Gong, Zheng-Yu Fang, Xiao-Feng Wu. Synthesis of quinazolinones from o-aminobenzamides and benzyl amines under metal-free conditions[J]. Chinese Chemical Letters,
;2016, 27(01): 21-24.
doi:
10.1016/j.cclet.2015.08.003
-
A convenient and transition-metal free protocol for quinazolinones synthesis with o-aminobenzamides and benzyl amines as substrates has been developed. Using H2O2 as the oxidant, various quinazolinones were obtained in moderate to good yields under metal-and additive-free conditions.
-
Keywords:
- Quinazolinones,
- Metal-free,
- Benzyl amine,
- H2O2
-
-
-
[1]
[1](a) S.B. Mhaske, N.P. Argade, The chemistry of recently isolated naturally occurring quinazolinone alkaloids, Tetrahedron 62(2006) 9787-9826;(b) D.A. Horton, G.T. Bourne, M.L. Smythe, The combinatorial synthesis of bicyclic privileged structures or privileged substructures, Chem. Rev. 103(2003) 893-930.
-
[2]
[2] A.K. Nanda, S. Ganguli, R. Chakraborty, antibacterial activity of some 3-(arylideneamino)-2-phenylquinazoline-4(3h)-ones:synthesis and preliminary QSAR Studies, Molecules 12(2007) 2413-2426.
-
[3]
[3](a) P.M. Chandrika, T. Yakaiah, A.R.R. Rao, et al., Synthesis of novel 4,6-disubstituted quinazoline derivatives, their anti-inflammatory and anti-cancer activity(cytotoxic) against U937 leukemia cell lines, Eur. J. Med. Chem. 43(2008) 846-852;(b) S.L. Cao, Y.P. Feng, Y.Y. Jiang, et al., Synthesis and in vitro antitumor activity of 4(3H)-quinazolinone derivatives with dithiocarbamate side chains, Bioorg. Med. Chem. Lett. 15(2005) 1915-1917;(c) M. Dupuy, F. Pinguet, O. Chavignon, et al., Synthesis and in vitro cytotoxic evaluation of new derivatives of pyrido[1,2-a]benzimidazolic ring system:the pyrido[1',2':1,2] imidazo[4,5-h]quinazolines, Chem. Pharm. Bull. 49(2001) 1061-1065;(d) Y. Takase, T. Saeki, N. Watanabe, et al., Cyclic GMP phosphodiesterase inhibitors. 2. Requirement of 6-substitution of quinazoline derivatives for potent and selective inhibitory activity, J. Med. Chem. 37(1994) 2106-2111.
-
[4]
[4] O. Kenichi, Y. Yoshihisa, O. Toyonari, I. Toru, I. Yoshio, Studies on 4(1h)-quinazolinones. 5. Synthesis and antiinflammatory activity of 4(1h)-quinazolinone derivatives, J. Med. Chem. 28(1985) 568-576.
-
[5]
[5] B.S. Kuarm, Y.T. Reddy, J.V. Madhav, P.A. Crooks, B. Rajitha, 3-[Benzimidazo]-and 3-[benzothiadiazoleimidazo-(1,2-c)quinazolin-5-yl]-2H-chromene-2-ones as potent antimicrobial agents, Bioorg. Med. Chem. Lett. 21(2011) 524-527.
-
[6]
[6] K. Waisser, J. Gregor, H. Dostal, et al., Influence of the replacement of the oxo function with the thioxo group on the antimycobacterial activity of 3-aryl-6,8-dichloro-2h-1,3-benzoxazine-2,4(3h)-diones and 3-arylquinazoline-2,4(1h, 3h)-diones, Farmaco 56(2001) 803-807.
-
[7]
[7] K. Tereshima, H. Shimamura, A. Kawase, et al., Studies on antiulcer agents. IV. Antiulcer effects of 2-benzylthio-5,6,7,8-tetrahydro-4(3h)-quinazolinones and related compounds, Chem. Pharm. Bull. 43(1995) 2021-2023.
-
[8]
[8](a) H. Kikuchi, K. Yamamoto, S. Horoiwa, et al., Exploration of a new type of antimalarial compounds based on febrifugine, J. Med. Chem. 49(2006) 4698-4706;(b) N. Malecki, P. Carato, G. Rigo, et al., Synthesis of condensed quinolines and quinazolines as DNA ligands, Bioorg. Med. Chem. 12(2004) 641-647;(c) K. Matsuno, J. Ushiki, T. Seishi, et al., Potent and selective inhibitors of plateletderived growth factor receptor phosphorylation. 3. Replacement of quinazoline moiety and improvement of metabolic polymorphism of 4-[4-(N-substituted(thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives, J. Med. Chem. 46(2003) 4910-4925.
-
[9]
[9] J.F. Liu, Rapid syntheses of biologically active quinazolinone natural products using microwave technology, Curr. Org. Syn. 4(2007) 223-237.
-
[10]
[10](a) L. He, H. Li, J. Chen, X.F. Wu, Recent advances in 4(3h)-quinazolinone syntheses, RSC Adv. 4(2014) 12065-12077;(b) W. Xu, Y. Jin, H. Liu, Y. Jiang, H. Fu, Copper-catalyzed domino synthesis of quinazolinones via ullmann-type coupling and aerobic oxidative C-H amidation, Org. Lett. 13(2011) 1274-1277;(c) W. Xu, H. Fu, Amino acids as the nitrogen-containing motifs in coppercatalyzed domino synthesis of N-heterocycles, J. Org. Chem. 76(2011) 3846-3852;(d) B.Q. Hu, L.X. Wang, J.F. Xiang, L. Yang, Y.L. Tang, Cu(Ⅱ)-catalyzed domino reaction of 2-halobenzamide and arylmethanamine to construct 2-aryl quinazolinone, Chin. Chem. Lett. 26(2015) 369-372;(e) M. Wang, T.T. Zhang, Z.G. Song, Eco-friendly synthesis of 2-substituted-2,3-dihydro-4(1h)-quinazolinones in water, Chin. Chem. Lett. 22(2011) 427-430;(f) M. Wang, Z.G. Song, T.T. Zhang, Strontium chloride-catalyzed one-pot synthesis of 4(3H)-quinazolinones under solvent-free conditions, Chin. Chem. Lett. 21(2010) 1167-1170;(g) C. Xie, H.X. Li, M.G. Liu, M.W. Ding, Efficient synthesis of 4(3h)-quinazolinones using a soluble polymeric support, Chin. Chem. Lett. 19(2008) 505-508.
-
[11]
[11] T.B. Nguyen, J.L. Bescont, L. Ermolenko, A. Al-Mourabit, Cobalt-and iron-catalyzed redox condensation of o-substituted nitrobenzenes with alkylamines:a step-and redox-economical synthesis of diazaheterocycles, Org. Lett. 15(2013) 6218-6221.
-
[12]
[12](a) A.J.A. Watson, A.C. Maxwell, J.M. Williams, Ruthenium-catalysed oxidative synthesis of heterocycles from alcohols, Org. Biomol. Chem. 10(2012) 240-243;(b) J. Zhou, J. Fang, One-pot synthesis of quinazolinones via iridium-catalyzed hydrogen transfers, J. Org. Chem. 76(2011) 7730-7736.
-
[13]
[13](a) T. Hisano, M. Ichikawa, A. Nakagawa, M. Tsuji, Studies on organosulfur compounds. Ⅻ. Syntheses and pharmacological activities of 2-heterocyclic substituted 4(3h)-quinazolinones, Chem. Pharm. Bull. 23(1975) 1910-1916;(b) R.J. Abdel-Jalil, H.M. Aldoqum, M.T. Ayoub, W. Voelter, Synthesis and antitumor activity of 2-aryl-7-fluoro-6-(4-methyl-1-piperazinyl)-4(3h)-quinazolinones, Heterocycles 65(2005) 2061-2070;(c) M. Bakavoli, A. Shiri, Z. Ebrahimpour, M. Rahimizadeh, Clean heterocyclic synthesis in water:I2/KI catalyzed one-pot synthesis of quinazolin-4(3h)-ones, Chin. Chem. Lett. 19(2008) 1403-1406;(d) C. Balakumar, P. Lamba, D.P. Kishore, et al., Synthesis, anti-inflammatory evaluation and docking studies of some new fluorinated fused quinazolines, Eur. J. Med. Chem. 45(2010) 4904-4913.
-
[14]
[14](a) T.B. Nguyen, L. Ermolenko, A. Al-Mourabit, Selective autoxidation of benzylamines:application to the synthesis of some nitrogen heterocycles, Green Chem. 15(2013) 2713-2717;(b) D. Mao, J. Tang, W. Wang, et al., A Sc(OTf)3-catalyzed cascade reaction of oaminoacetophenone with methanamine:construction of dibenzo[b,h][1,6]-naphthyridine derivatives, Org. Biomol. Chem. 13(2015) 2122-2128;(c) D. Mao, J. Tang, W. Wang, et al., Scandium pentafluorobenzoate-catalyzed unexpected cascade reaction of 2-aminobenzaldehydes with primary amines:a process for the preparation of ring-fused aminals, J. Org. Chem. 78(2013) 12848-12854.
-
[15]
[15] X.F. Wu, A. Petrosyan, T.V. Ghochikyan, A.S. Saghyan, P. Langer, Metal-free oxidation of benzyl amines to imines, Tetrahedron Lett. 54(2013) 3158-3159.
-
[1]
-
-
-
[1]
Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
-
[2]
Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp3)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
-
[3]
Xiaodan Wang , Yingnan Liu , Zhibin Liu , Zhongjian Li , Tao Zhang , Yi Cheng , Lecheng Lei , Bin Yang , Yang Hou . Highly efficient electrosynthesis of H2O2 in acidic electrolyte on metal-free heteroatoms co-doped carbon nanosheets and simultaneously promoting Fenton process. Chinese Chemical Letters, 2024, 35(7): 108926-. doi: 10.1016/j.cclet.2023.108926
-
[4]
Jianhui Yin , Wenjing Huang , Changyong Guo , Chao Liu , Fei Gao , Honggang Hu . Tryptophan-specific peptide modification through metal-free photoinduced N-H alkylation employing N-aryl glycines. Chinese Chemical Letters, 2024, 35(6): 109244-. doi: 10.1016/j.cclet.2023.109244
-
[5]
Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
-
[6]
Jie Li , Huida Qian , Deyang Pan , Wenjing Wang , Daliang Zhu , Zhongxue Fang . Efficient Synthesis of Anethaldehyde Induced by Visible Light. University Chemistry, 2024, 39(4): 343-350. doi: 10.3866/PKU.DXHX202310076
-
[7]
Xin Li , Wanting Fu , Ruiqing Guan , Yue Yuan , Qinmei Zhong , Gang Yao , Sheng-Tao Yang , Liandong Jing , Song Bai . Nucleophiles promotes the decomposition of electrophilic functional groups of tetracycline in ZVI/H2O2 system: Efficiency and mechanism. Chinese Chemical Letters, 2024, 35(10): 109625-. doi: 10.1016/j.cclet.2024.109625
-
[8]
Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H2O2 for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
-
[9]
Cailiang Yue , Nan Sun , Yixing Qiu , Linlin Zhu , Zhiling Du , Fuqiang Liu . A direct Z-scheme 0D α-Fe2O3/TiO2 heterojunction for enhanced photo-Fenton activity with low H2O2 consumption. Chinese Chemical Letters, 2024, 35(12): 109698-. doi: 10.1016/j.cclet.2024.109698
-
[10]
Jing Wang , Zhongliao Wang , Jinfeng Zhang , Kai Dai . Single-layer crystalline triazine-based organic framework photocatalysts with different linking groups for H2O2 production. Chinese Journal of Structural Chemistry, 2023, 42(12): 100202-100202. doi: 10.1016/j.cjsc.2023.100202
-
[11]
Zhenyu Hu , Zhenchun Yang , Shiqi Zeng , Kun Wang , Lina Li , Chun Hu , Yubao Zhao . Cationic surface polarization centers on ionic carbon nitride for efficient solar-driven H2O2 production and pollutant abatement. Chinese Chemical Letters, 2024, 35(10): 109526-. doi: 10.1016/j.cclet.2024.109526
-
[12]
Hao Lv , Zhi Li , Peng Yin , Ping Wan , Mingshan Zhu . Recent progress on non-metallic carbon nitride for the photosynthesis of H2O2: Mechanism, modification and in-situ applications. Chinese Chemical Letters, 2025, 36(1): 110457-. doi: 10.1016/j.cclet.2024.110457
-
[13]
Sikai Wu , Xuefei Wang , Huogen Yu . Hydroxyl-enriched hydrous tin dioxide-coated BiVO4 with boosted photocatalytic H2O2 production. Chinese Journal of Structural Chemistry, 2024, 43(12): 100457-100457. doi: 10.1016/j.cjsc.2024.100457
-
[14]
Chunxiu Yu , Zelin Wu , Hongle Shi , Lingyun Gu , Kexin Chen , Chuan-Shu He , Yang Liu , Heng Zhang , Peng Zhou , Zhaokun Xiong , Bo Lai . Insights into the electron transfer mechanisms of peroxydisulfate activation by modified metal-free acetylene black for degradation of sulfisoxazole. Chinese Chemical Letters, 2024, 35(8): 109334-. doi: 10.1016/j.cclet.2023.109334
-
[15]
Lang Gao , Cen Zhou , Rui Wang , Feng Lan , Bohang An , Xiaozhou Huang , Xiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832
-
[16]
Xiuwen Xu , Quan Zhou , Yacong Wang , Yunjie He , Qiang Wang , Yuan Wang , Bing Chen . Expanding the toolbox of metal-free organic halide perovskite for X-ray detection. Chinese Chemical Letters, 2024, 35(9): 109272-. doi: 10.1016/j.cclet.2023.109272
-
[17]
Kexin Yin , Jingren Yang , Yanwei Li , Qian Li , Xing Xu . Metal-free diatomaceous carbon-based catalyst for ultrafast and anti-interference Fenton-like oxidation. Chinese Chemical Letters, 2024, 35(12): 109847-. doi: 10.1016/j.cclet.2024.109847
-
[18]
Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H2O2 Production and Cr(VI) Reduction over a Hierarchical Ti3C2/In4SnS8 Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
-
[19]
Xinyu Yin , Haiyang Shi , Yu Wang , Xuefei Wang , Ping Wang , Huogen Yu . Spontaneously Improved Adsorption of H2O and Its Intermediates on Electron-Deficient Mn(3+δ)+ for Efficient Photocatalytic H2O2 Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312007-. doi: 10.3866/PKU.WHXB202312007
-
[20]
Zhenchun Yang , Bixiao Guo , Zhenyu Hu , Kun Wang , Jiahao Cui , Lina Li , Chun Hu , Yubao Zhao . Molecular engineering towards dual surface local polarization sites on poly(heptazine imide) framework for boosting H2O2 photo-production. Chinese Chemical Letters, 2024, 35(8): 109251-. doi: 10.1016/j.cclet.2023.109251
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(704)
- HTML views(14)