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Document Type : Original Article

Authors

1 Department of Chemistry, Payame Noor University, PO Box 19395‑4697, Tehran, Iran

2 Department of Chemistry, Ayatollah Alozma Borujerdi University, Borujerd, Iran

Abstract

MOF-5 has been employed as a powerful catalyst for the preparation of 2-amino-4H-chromene. A wide variety of aromatic aldehydes was condensed with malononitrile and 2-naphthol under mild and solvent-free conditions in the presence of the trace amount of catalyst. A variety of 2-amino-4H-chromene can be obtained in good to excellent yield up to 95% in relatively short time reaction and easy workup.

Graphical Abstract

Synthesis of 2-Amino-4H-chromene Derivatives under Solvent-Free Condition Using MOF-5

Keywords

Main Subjects

[1] Martínez-Grau A., Marco J. Bioorg. Med. Chem. Lett., 1997, 7:3165
[2] Khafagy M.M., El-Wahas A.H.F.A., Eid F.A., El-Agrody A.M. IL Farma., 2002, 57:715
[3] Dell C.P., Smith C.W. European Patent Appl. EP 537949, Chem. Abstr., 1993, 119139102d
[4] Hiramoto K., Nasuhara A., Michiloshi K., Kato T., Kikugawa K. Mutat. Res., Genet. Toxicol. Environ. Mutagen., 1997, 395:47
[5] Mohr S.J., Chirigos M.A., Fuhrman F.S., Pryor J.W. Cancer Res., 1975, 35:3750
[6] Bianchi G., Tavaz A. Agric. Biol. Chem., 1987, 51:2001
[7] Anderson D.R., Hegde S., Reinhard E., Gomez L., Vernier W.F., Lee L., Liu S., Sambandam A., Snider P.A., Masih L. Bioorg. Med. Chem. Lett., 2005, 15:1587
[8] Kalla R.M.N., Byeon S.J., Heo M.S., Kim I. Tetrahedron, 2013, 69:10544
[9] Safari J., Zarnegar Z. J. Mol. Struct., 2014, 1072:53
[10] Kumar B.S., Srinivasulu N., Udupi R.H., Rajitha B., Reddy Y.T., Reddy P.N., Kumar P.S. J. Heterocyclic Chem., 2006, 43:1691
[11] Lakshmi N.V., Kiruthika S.E., Perumal P.T. Synlett, 2011, 2011:1389
[12] Kale S.R., Kahandal S.S., Burange A.S., Gawandeb M.B., Jayaram R.V. Catal. Sci. Technol., 2013, 3:2050
[13] Dekamin M.G., Eslami M., Maleki A. Tetrahedron, 2013, 69:1074
[14] Zolfigol M.A., Yarie M., Baghery S. Synlett, 2016, 27:1418
[15] Heravi M.M., Baghernejad B., Oskooie H.A. J. Chin. Chem. Soc., 2008, 55:659
[16] Vangala V.B., Pati H. Chem. Method., 2018, 2:333
[17] Behbahani F.K., Shahbazi R. Chem. Method., 2018, 2:270
[18] Momeni A.R., Samimi H., Vaezzadeh H. Chem. Method., 2018, 2:260
[19] Samadi S., Behbahani F.K. Chem. Method., 2018, 2:181
[20] Shaikh U.U., Tamboli Q.Y, Pathange S.M., Dahan Z.A., Pudukulathan Z. Chem. Method., 2018, 2:73
[21] Salavati H., Teimouri A., Kazemi S. Chem. Method., 2017, 1:145
[22] Sajjadifar S. Chem. Method., 2017, 1:1
[23] Salavati H., Teimouri A., Kazemi S. Chem. Method., 2017, 1:12
[24] Chughtai A.H., Ahmad N., Younus H.A., Laypkov A., Verpoort F. Chem. Soc. Rev., 2015, 44:6804
[25] Soleiman-Beigi M., Arzehgar Z. J. Sulfur Chem., 2015, 36:395
[26] Soleiman-Beigi M., Arzehgar Z., Movassagh B.‏ Synthesis, 2010, 2010:392
[27] Soleiman‐Beigi M., Arzehgar Z. Heteroatom Chem., 26:355
[28] Soleiman-Beigi M., Arzehgar Z.‏ Monatsh Chem., 2016, 147:1759
[29] Sajjadifar S., Rezayati S., Arzehgar Z., Abbaspour S., Torabi Jafroud M. J. Chin. Chem. Soc., 2018, 65:960
[30] Dhakshinamoorthy A., Asiric A.M., Garcia H. Chem. Soc. Rev., 2015, 44:1922
[31] Soleiman-Beigi M., Yavari I., Sadeghizadeh F. RSC. Adv., 2015, 5:87564
[32] Sajjadifar S., Arzehgar Z., Ghayuri A. J. Chin. Chem. Soc., 65:205
[33] Soleiman-Beigi M., Arzehga Z. Synlett, 2018, 29:986
[34] Sajjadifar S., Arzehgar Z., Khoshpoori S. J. Inorg. Organomet. Polym. Mater., 2018, 28:837
[35] Arzehgar Z., Sajjadifar S., Arandiyan H. Asian J. Green Chem., 2019, 3:43
[36] Li J., Cheng S., Zhao Q., Long P., Dong J. Int. J. Hydrogen. Energy, 2009, 34:1377
[37] Kumar D., Reddy V.B., Mishra B.G., Rana R.K., Nadagouda M.N., Varma R.S. Tetrahedron, 2007, 63:3093
[38] Safari J., Zarnegar Z. J. Mol. Struct., 2014, 1072:53
[39] Kundu S.K., Mondal J., Bhaumi A. Dalton Trans., 2013, 42:10515
[40] Akocak S., Şen B., Lolak N., Şavk A., Koca M., Kuzu S., Şen F. Nano-Struct. Nano-Object., 2017, 11:25
[41] Eshghi H., Damavandi S., Zohuri G.H. Synth. React. Inorg. Met., 2011, 41:1067
[42] Kundu S.K., Bhaumik A. Rsc. Adv., 2015, 5:32730