Cetyltrimethylammonium chloride (CTAC) catalyzed one-pot synthesis of novel coumarin-4H-pyran conjugates in aqueous media
- Corresponding author: Ablajan Keyume, ablajan209@hotmail.com
Citation:
Omar Adil, Ablajan Keyume, Hamdulla Mawjvda. Cetyltrimethylammonium chloride (CTAC) catalyzed one-pot synthesis of novel coumarin-4H-pyran conjugates in aqueous media[J]. Chinese Chemical Letters,
;2017, 28(5): 976-980.
doi:
10.1016/j.cclet.2016.12.016
Abenavoli M.R., Santis C.D., Sidari M.. Influence of coumarin on the net nitrate uptake in durum wheat[J]. New Phytol., 2001(150):619-627.
Hwang C.H., Jaki B.U., Klein L.L.. Chlorinated coumarins from the polypore mushroom Fomitopsis officinalis and their activity against Mycobacterium tuberculosis[J]. J. Nat. Prod., 2013(76):1916-1922.
Li Y., Zhang T., Schwartz S.J., Sun D.. New developments in Hsp90 inhibitors as anti-cancer therapeutics:mechanisms. clinical perspective and more potential[J]. Drug Resist. Update, 2009(12):17-27.
Fylaktakidou K.C., Ke H.L.D., Nicolaides D.N.. Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities[J]. Curr. Pharm. Des., 2004(10):3813-3833.
Sardari S., Mori Y., Horita K.. Synthesis and antifungal activity of coumarins and angular furanocoumarins[J]. Bioorg. Med. Chem., 1999(7):1933-1940.
Amin K.M., Awadalla F.M., Eissa A.A.M., Abou-Seri S.M., Hassan G.S.. Design. synthesis and vasorelaxant evaluation of novel coumarin-pyrimidine[J]. Bioorg. Med. Chem., 2011(19):6087-6097.
Rost S., Fregin A., Ivaskevicius V.. Mutations in VKORC1 cause warfarin resistance and multiple coagulation factor deficiency type 2[J]. Nature, 2004(427):537-541.
Wang T., Wang C., Zhou N., Pan X., He H.. Synthesis and vasorelaxation evaluation of novel biphenyl-furocoumarin derivatives[J]. Med. Chem. Res., 2015(24):2417-2431.
Gupta V.K., Mergu N., Kumawat L.K., Singh A.K.. Selective naked-eye detection of magnesium (Ⅱ) ions using a coumarin-derived fluorescent probe[J]. Sens. Actuators B:Chem., 2015(207):216-223.
Yoo M., Park S., Kim H.J.. Highly selective detection of cyanide by 2-hydroxyphenylsalicylimine of latent fluorescence through the cyanidecatalyzed imine-to-oxazole transformation[J]. Sens. Actuators B:Chem., 2015(220):788-793.
Wang H., Guo L.E., Li X.M.. Coumarin-based turn-on fluorescence probes for highly selective detection of Pi in cell culture and Caenorhabditis elegans[J]. Dyes Pigments, 2015(120):293-298.
Ye D., Wang L., Li H., Zhou J., Cao D.. Synthesis of coumarin-containing conjugated polymer for naked-eye detection of DNA and cellular imaging[J]. Sens. Actuators B:Chem., 2013(181):234-243.
Sarwar T., Rehman S.U., Husain M.A., Ishqi H.M., Tabish M.. Interaction of coumarin with calf thymus DNA:deciphering the mode of binding by in vitro studies[J]. Int. J. Biol. Macromol., 2015(73):9-16.
Zhu S., Lin W., Yuan L.. Development of a ratiometric fluorescent pH probe for cell imaging based on a coumarin-quinoline platform[J]. Dyes Pigments, 2013(99):465-471.
Gu Y.. Multicomponent reactions in unconventional solvents:state of the art[J]. Green Chem., 2012(14):2091-2128.
Hernández F., Sánchez A., Rendón-Vallejo P.. Synthesis. ex vivo and in silico studies of 3-cyano-2-pyridone derivatives with vasorelaxant activity[J]. Eur. J. Med. Chem., 2013(70):669-676.
Wang J.L., Liu D., Zhang Z.J.. Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells[J]. Proc. Natl. Acad. Sci. U. S. A., 2000(97):7124-7129.
Li J., Sui Y.P., Xin J.J.. Synthesis of biscoumarin and dihydropyran derivatives with promising antitumor and antibacterial activities[J]. Bioorg. Med. Chem. Lett., 2015(25):5520-5523.
Kamatchi T.S., Kalaivani P., Poornima P.. New organometallic ruthenium (ii) complexes containing chelidonic acid (4-oxo-4H-pyran-2, 6-dicarboxylic acid):synthesis. structure and in vitro biological activity[J]. RSC Adv., 2014(4):2004-2022.
Giblin G.M., O'Shaughnessy C.T., Naylor A.. Discovery of 2-[(2, 4-dichlorophenyl) amino]-N-[(tetrahydro-2H-pyran-4-yl)methyl]-4-(trifluoromethyl)-5-pyrimidinecarboxamide. a selective CB2 receptor agonist for the treatment of inflammatory pain[J]. J. Med. Chem., 2007(50):2597-2600.
Dömling A.. Recent developments in isocyanide based multicomponent reactions in applied chemistry[J]. Chem. Rev., 2006(106):17-89.
Liju W., Ablajan K., Jun F.. Rapid and efficient one-pot synthesis of spiro[indoline-3, 4'-pyrano[2.3-c] pyrazole] derivatives catalyzed by L-proline under ultrasound irradiation[J]. Ultrason. Sonochem., 2015(22):113-118.
Keyume A., Esmayil Z., Wang L., Jun F.. Convenient DABCO-catalyzed one-pot synthesis of multi-substituted pyrano[2.3-c] pyrazole dicarboxylates[J]. Tetrahedron, 2014(70):3976-3980.
Nanayakkara Y.S., Armstrong D.W.. A liquid drop RC filter apparatus for detection[J]. Anal. Bioanal. Chem., 2011(401):2669-2678.
Reddy K.R., Rajanna K., Uppalaiah K.. Environmentally benign contemporary Friedel-Crafts acylation of 1-halo-2-methoxy naphthalenes and its related compounds under conventional and nonconventional conditions[J]. Tetrahedron Lett., 2013(54):3431-3436.
Jin T.S., Xiao J.C., Wang S.J., Li T.S.. Ultrasound-assisted synthesis of 2-amino-2-chromenes with cetyltrimethylammonium bromide in aqueous media[J]. Ultrason. Sonochem., 2004(11):393-397.
Albanese D., Donghi A., Landini D., Lupi V., Penso M.. Environmentally benign sequential synthesis of 3, 4-dihydro-2H-1.4-benzoxazines under phase transfer catalysis conditions[J]. Green Chem., 2003(5):367-369.
Ablajan K., Liju W., Tuoheti A., Kelimu Y.. An efficient four-component one-pot synthesis of 6-amino-4-aryl-3-methyl-2, 4-dihydropyrano[2.3-C] pyrazole-5-carbonitriles under phase-transfer catalyst[J]. Lett. Org. Chem., 2012(9):639-643.
Benazzouz A., Makhloufi-Chebli M., Khatir-Hamdi N.. A facile synthesis of new coumarin-3.4-dihydropyrimidin-2(1H)-ones/thiones dyads[J]. Tetrahedron, 2015(71):3890-3894.
Ghosh P.P., Pal G., Paul S., Das A.R.. Design and synthesis of benzylpyrazolyl coumarin derivatives via a four-component reaction in water:investigation of the weak interactions accumulating in the crystal structure of a signified compound[J]. Green Chem., 2012(14):2691-2698.
Wang H., Liu X., Feng X., Huang Z., Shi D.. GAP chemistry for pyrrolyl coumarin derivatives:a highlyefficientone-potsynthesis undercatalyst-freeconditions[J]. Green Chem., 2013(15):3307-3311.
Vitório F., Pereira T.M., Castro R.N.. Synthesis and mechanism of novel fluorescent coumarin-dihydropyrimidinone dyads obtained by the Biginelli multicomponent reaction[J]. New J. Chem., 2015(39):2323-2332.
Sugino T., Tanaka K.. Solvent-free coumarin synthesis[J]. Chem. Lett., 2001(11):110-111.
Gawande M.B., Bonifacio V.D.B., Luque R., Branco P.S., Varma R.S.. Benign by design:catalyst-free in-water. on-water green chemical methodologies in organic synthesis[J]. Chem. Soc. Rev., 2013(42):5522-5551.
Li D., Li H., Fu Y.. Critical micelle concentrations of cetyltrimethylammonium chloride and their influence on the periodic structure of mesoporous silica[J]. Colloid J., 2008(70):747-752.
Yingying Yan , Wanhe Jia , Rui Cai , Chun Liu . An AIPE-active fluorinated cationic Pt(Ⅱ) complex for efficient detection of picric acid in aqueous media. Chinese Chemical Letters, 2024, 35(5): 108819-. doi: 10.1016/j.cclet.2023.108819
Junying Zhang , Ruochen Li , Haihua Wang , Wenbing Kang , Xing-Dong Xu . Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media. Chinese Chemical Letters, 2024, 35(6): 109216-. doi: 10.1016/j.cclet.2023.109216
Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
Jian Han , Li-Li Zeng , Qin-Yu Fei , Yan-Xiang Ge , Rong-Hui Huang , Fen-Er Chen . Recent advances in remote C(sp3)–H functionalization via chelating group-assisted metal-catalyzed chain-walking reaction. Chinese Chemical Letters, 2024, 35(11): 109647-. doi: 10.1016/j.cclet.2024.109647
Yi Luo , Lin Dong . Multicomponent remote C(sp2)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C6F5)3/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
Yiqian Jiang , Zihan Yang , Xiuru Bi , Nan Yao , Peiqing Zhao , Xu Meng . Mediated electron transfer process in α-MnO2 catalyzed Fenton-like reaction for oxytetracycline degradation. Chinese Chemical Letters, 2024, 35(8): 109331-. doi: 10.1016/j.cclet.2023.109331
Yi-Fan Wang , Hao-Yun Yu , Hao Xu , Ya-Jie Wang , Xiaodi Yang , Yu-Hui Wang , Ping Tian , Guo-Qiang Lin . Rhodium(Ⅲ)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α, β-unsaturated aldehydes. Chinese Chemical Letters, 2024, 35(9): 109520-. doi: 10.1016/j.cclet.2024.109520
Shuai Zhu , Mingjie Chen , Haichao Shen , Hanming Ding , Wenbo Li , Junliang Zhang . Palladium/Xu-Phos-catalyzed enantioselective arylalkoxylation reaction of γ-hydroxyalkenes at room temperature. Chinese Chemical Letters, 2024, 35(11): 109879-. doi: 10.1016/j.cclet.2024.109879
Hongliang Zeng , Yuan Ji , Jinfeng Wen , Xu Li , Tingting Zheng , Qiu Jiang , Chuan Xia . Pt nanocluster-catalyzed hydrogen evolution reaction: Recent advances and future outlook. Chinese Chemical Letters, 2025, 36(3): 109686-. doi: 10.1016/j.cclet.2024.109686
Xinghui Yao , Zhouyu Wang , Da-Gang Yu . Sustainable electrosynthesis: Enantioselective electrochemical Rh(III)/chiral carboxylic acid-catalyzed oxidative CH cyclization coupled with hydrogen evolution reaction. Chinese Chemical Letters, 2024, 35(9): 109916-. doi: 10.1016/j.cclet.2024.109916
Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp3)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
Jingjing Zhang , Lan Ding , Vadim Popkov , Kezhen Qi . Aqueous indium metal batteries. Chinese Chemical Letters, 2025, 36(2): 110407-. doi: 10.1016/j.cclet.2024.110407
Guang Xu , Cuiju Zhu , Xiang Li , Kexin Zhu , Hao Xu . Copper-catalyzed asymmetric [4+1] annulation of yne–allylic esters with pyrazolones. Chinese Chemical Letters, 2025, 36(4): 110114-. doi: 10.1016/j.cclet.2024.110114
Pengfei Zhang , Qingxue Ma , Zhiwei Jiang , Xiaohua Xu , Zhong Jin . Transition-metal-catalyzed remote meta-C—H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template. Chinese Chemical Letters, 2024, 35(8): 109361-. doi: 10.1016/j.cclet.2023.109361
Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
Hong-Tao Ji , Yu-Han Lu , Yan-Ting Liu , Yu-Lin Huang , Jiang-Feng Tian , Feng Liu , Yan-Yan Zeng , Hai-Yan Yang , Yong-Hong Zhang , Wei-Min He . Nd@C3N4-photoredox/chlorine dual catalyzed synthesis and evaluation of antitumor activities of 4-alkylated sulfonyl ketimines. Chinese Chemical Letters, 2025, 36(2): 110568-. doi: 10.1016/j.cclet.2024.110568
Yi Herng Chan , Zhe Phak Chan , Serene Sow Mun Lock , Chung Loong Yiin , Shin Ying Foong , Mee Kee Wong , Muhammad Anwar Ishak , Ven Chian Quek , Shengbo Ge , Su Shiung Lam . Thermal pyrolysis conversion of methane to hydrogen (H2): A review on process parameters, reaction kinetics and techno-economic analysis. Chinese Chemical Letters, 2024, 35(8): 109329-. doi: 10.1016/j.cclet.2023.109329