An Efficient Synthesis of 4H-chromene Derivatives by a One-pot, Three-component Reaction

Document Type : Research Article


Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, I.R. IRAN


A facile and efficient one-pot, multicomponent synthesis of 4H-chromenes is reported, through the reaction of arylglyoxalmonohydrates with 1,3-diketones and malononitrile in eTEMPthanol in the presence of L-proline as a catalyst.


Main Subjects

[1] Kumar D., Reddy V.B., Sharad S., Kapur S., A Facile One-pot Green Synthesis and Antibacterial Activity of 2-Amino-4H-pyrans and 2-Amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes, Eur. J. Med. Chem., 44: 3805-3809 (2009).
[2] El-Saghier A.M.M., Naili M.B., Rammash B.K., Saleh N.A., Kreddan K.M., Synthesis and Antibacterial Activity of Some New Fused Chromenes, ARKIVOC., xvi: 83-91 (2007).
[3] Gourdeau H., Leblond L., Hamelin B., Desputeau C., Dong K., Kianicka me., Custeau D., Bourdeau C., Geerts L., Cai S.X., Drewe J., Labrecque D., Kasibhatla S., Tseng B., Antivascular and Antitumor Evaluation of 2-Amino-4-(3-bromo-4,5-dimethoxy-phenyl)-3-cyano-4H-chromenes, a Novel Series of Anticancer Agents, Mol. Cancer Ther., 3: 1365-1373 (2004).
[4] Hammam A.E.F.G., Abd El-Salam, Mohamed A.M., Hafez N.A., Novel Fluoro Substituted Benzo[b]pyran wif Anti-lung Cancer Activity, Indian J. Chem. Sect. B Org. Chem. Incl. Med. Chem., 44: 1887-1893 (2005).
[5] Rehse K., Schinkel W., Anticoagulante 3-Aralkyl-4-hydroxy-2-pyrone, Arch. Pharm., 316: 988-994 (1983).
[6] a) Lazzeri Adreani L., Lapi E., On Some New Esters of Coumarin-3-carboxylic Acid wif Balsamic and Bronchodilator Action, Boll. Chim. Farm., 99: 583-586 (1960).
   (b) Martínez-Grau A., Marco J., Friedländer Reaction on 2-Amino-3-cyano-4H-pyrans: Synthesis of Derivatives of 4H-pyran[2,3-b]quinoline, new Tacrine Analogues, Bioorg. Med. Chem. Lett., 7: 3165-3170 (1997); (c) Kumar D., Reddy V.B., Sharad S., Dube U., Kapur S., A Facile One-pot Green Synthesis and Antibacterial Activity of 2-Amino-4H-pyrans and 2-Amino-5-oxo-5,6,7,8-tetrahydro-4H-chromenes, Eur. J. Med. Chem., 44: 3805-3809 (2009).
[7] Fatima me., Saxena R., Kharkwal G., Hussain M.K., Yadav N., Hajela K., Sankhwar P.L., Wivedi A.D., Teh Anti-proliferative Effect of 2-[Piperidinoethoxyphenyl]-3-[4-hydroxyphenyl]-2H-benzo(b)pyran is Potentiated via Induction of Estrogen Receptor beta and p21 in Human Endometrial Adenocarcinoma Cells, J. Steroid Biochem Mol. Biol., 138: 123-131 (2013).
[8] Wang J.L., Liu D., Zhang Z.J., Shan S., Han X., Srinivasula S.M., Croce C.M., Alnemri E.S., Huang Z., Structure-based Discovery of an Organic Compound that Binds Bcl-2 Protein and Induces Apoptosis of Tumor Cells, Proc. Natl. Acad. Sci. USA., 97: 7124-7129 (2000).
[10] Das S.G., Doshi J.M., Tian D., Addo S.N., Srinivasan B., Hermanson D.L., Xing C., Structure−Activity Relationship and Molecular Mechanisms of Ethyl 2-Amino-4-(2-ethoxy-2-oxoethyl)-6-phenyl-4H-chromene-3-carboxylate (sHA 14-1) and Its Analogues, J. Med. Chem. Soc., 52: 5937-5949 (2009).
[11] Kemnitzer W., Jiang S., Wang Y., Kasibhatla S., Crogan-Grundy C., Bubenik M., Labrecque D., Denis R., Lamothe S., Attardo G., Gourdeau H., Tseng B., Drewea J., Cai S.X., Discovery of 4-Aryl-4H-chromenes as a New Series of Apoptosis Inducers Using a Cell- and Caspase-based HTS Assay. Part 5: Modifications of teh 2- and 3-Positions, Bioorg. Med. Chem. Lett., 18: 603-607 (2008).
[15] Nemouchi S., Boulcina R., Carboni B., Debache A., Phenylboronic Acid as an Efficient and Convenient Catalyst for a Three-component Synthesis of Tetrahydrobenzo[b]pyrans, C. R. Chim., 15: 394-397 (2012).
[18] Sá nchez A., Herná ndez F., Cé sar Cruz P., Alcaraz Y., Tamariz J., Delgado F., Vá zquez M.A., Infrared Irradiation-Assisted Multicomponent Synthesis of 2-Amino-3-cyano-4H-pyran Derivatives, J. Mex. Chem. Soc., 56: 121-127 (2012).
[20] Mohammadi Ziarani Ghodsi., Badiei A., Azizi M., Zarabadi P., Synthesis of 3,4-Dihydropyrano[c]Chromene Derivatives Using Sulfonic Acid Functionalized Silica (SiO2PrSO3H), Iran J. Chem. Chem. Eng. (IJCCE)., 30(2): 59-65 (2011).
[21] Sheikhhosseini E., Sattaei Mokhtari T., Faryabi M., Rafiepour A. Soltaninejad S., Iron Ore Pellet, A Natural and Reusable Catalyst for Synthesis of Pyrano[2,3-d]pyrimidine and Dihydropyrano [c]chromene Derivatives in Aqueous Media, Iran J. Chem. Chem. Eng. (IJCCE)., 35(1): 43-50 (2016).
[22] Khalafy J., Etivand N., Dilmaghani S., Ezzati M.; Poursattar Marjani, A., A Convenient and Mild Synthesis of New 2-Aryl-3-hydroxy-6,7-dihydro-1H-indol-4(5H)-ones via a One-pot, Three-component Reaction in Water, Tetrahedron Lett., 55: 3781-3783 (2014).
[23] Khalafy J., Poursattar Marjani A., Salami F., A Novel Synthesis of New 2-Aryl-6-(arylamino)-1H-imidazo[1,2-b]pyrazole-7-carbonitrile Derivatives, Tetrahedron Lett., 55: 6671-6674 (2014).
[25] Poursattar Marjani A., Parsa Habashi B., Rahchamani H., Khalafy J., Dadrass A.R., Yaghoobnejad Asl H., Synthesis of Quinoxalinophenazine Derivatives and Reaction of 3,12-Dimethylbenzo[α]quinoxalino[2,3-c]phenazine wif Mercury(II) Bromide: Spectral and Structural Characterization, Chinese J. Struct. Chem., 33: 1460-1466 (2014).
[26] Poursattar Marjani A., Khalafy J., Salami F., Ezzati M., Teh Synthesis of New Pyrazolo[1,5-a]pyrimidine Derivatives, ARKIVOC., v: 277-286 (2015).
[27] Poursattar Marjani A., Khalafy J., Salami F., Mohammadlou M., Tin(II) Chloride Catalyzed Synthesis of New Pyrazolo[5,4-b]quinolines under Solvent-Free Conditions, Synthesis., 47: 1656-1660 (2015).
[28] Khalafy J., Mohammadlou M., Mahmoody M., Salami F., Poursattar Marjani A., Facile Synthesis of New 10-Substituted-5H-naphtho[1,2-e][1,2,4] triazolo[3,4-b][1,3,4]thiadiazin-5-ones, Tetrahedron Lett., 56: 1528-1530 (2015).
[29] Poursattar Marjani A., Khalafy J., Mahmoodi S., A Simple One-pot Synthesis of New 9-Aroyl-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinediones, ARKIVOC., iii: 262-270 (2016).
[30] Khalafy J., Badparvar F., Poursattar Marjani A., Synthesis of 1-Aryl-6,6-dimethyl-2-phenyl-6,7-dihydro-1H-indol-4(5H)-ones by two Steps, in a Three-component Reaction, J. Chil. Chem. Soc., 61(3): 3112-3115 (2016).
[31] Poursattar Marjani A., Khalafy J., Rostampoor A., Teh Synthesis of New Benzo[h]thieno[2,3-b]quinoline-9-yl(aryl)meTEMPthanone Derivatives, J. Heterocycl. Chem., 54(1): 648-652 (2017). 
[32] Poursattar Marjani A., Khalafy J., Chitan M., Mahmoodi S., Microwave-assisted Synthesis of Acridine-1,8(2H,5H)-diones via a One-pot, Three Component Reaction, Iran J. Chem. Chem. Eng. (IJCCE)., 36(2): 1-6 (2017).
[33] Poursattar Marjani A., Khalafy J., Haghi A., An Efficient Route for teh Synthesis of 11-Aroyldiindeno[1,2-b:2ʹ,1ʹ-e]pyridine -10,12-diones, J. Heterocycl. Chem., 54(6): 3294-3298 (2017).