Effective and convenient synthesis of 2-amino-4H-chromenes promoted by melamine as a recyclable organocatalyst

Kamali, Fatemeh; Shirini, Farhad

doi:10.22034/ecc.2021.272326.1136

Document Type : Original Research Article

Authors

Department of Chemistry, College of Science, University of Guilan, Zip Code 41335, Rasht, Iran

https://doi.org/10.22034/ecc.2021.272326.1136

Abstract

This study focused on the applicability of melamine as a cheap and efficient organocatalyst in the acceleration of the synthesis of 4-aryl-4H-chromenes derivatives. Under the selected conditions, a wide range of aldehydes readily underwent condensation with activated phenols and malononitrile to afford the high to excellent yields. Also, organocatalyst was used for the synthesis of 2-amino-5,10-dioxo-5,10-dihydro-4H-benzo[g]chromenes by the reaction of aromatic aldehydes, malononitrile and 2-hydroxynaphthalene-1,4-dione in refluxing H₂O:EtOH. This method provides several advantages such as convenient work-up, mild reaction conditions, use of an inexpensive and readily available catalyst, short reaction times, high yields of the products and reusability of the catalyst.

Graphical Abstract

Keywords

Main Subjects

Catalyst

References

[1] I.T. Horvath, P.T. Anastas, Chem. Rev., 2007, 107, 2169-2173. [crossref], [Google Scholar], [Publisher]

[2] B. Jiang, T. Rajale, W. Wever, S.J. Tu, G. Li, Chem Asian J., 2010, 5, 2318-2335. [crossref], [Google Scholar], [Publisher]

[3] A. DomLing, W. Wang, K. Wang, Chem. Rev., 2012, 112, 3083-3135. [crossref], [Google Scholar], [Publisher]

[4] M.M. Heravi, N. Karimi, S. Pooremami, Adv. J. Chem. A., 2019, 2, 73-78. [crossref], [Google Scholar], [Publisher]

[5] M.M. Heravi, H. Hamidi, N. Karimi, A. Amouchi, Adv. J. Chem. A., 2018, 1, 1-6. [crossref], [Google Scholar], [Publisher]

[6] K. Tanaka, F. Toda, Chem. Rev., 2000, 100, 1025–1074. [crossref], [Google Scholar], [Publisher]

[7] H.C. Hailes, Org. Process Res. Dev.,2007, 11, 114-120. [crossref], [Google Scholar], [Publisher]

[8] N.A. Mirgane, A.V. Karnik, Green Chem Lett Rev.,2011, 4, 269-272. [crossref], [Google Scholar], [Publisher]

[9] R.A. Sheldon, ChemComm., 2008, 29, 3352-3365. [crossref], [Google Scholar], [Publisher]

[10] G. Centi, S. Perathoner, Catal. Today., 2003, 77, 287-297. [crossref], [Google Scholar], [Publisher]

[11] B. List, Chem. Rev., 2007, 107, 5413-5415. [crossref], [Google Scholar], [Publisher]

[12] B.R. Buckley, M.C. Kimber, N.H. Slater, Annu. Rep. Prog. Chem., Sect. B: Org. Chem., 2012, 108, 98-109. [crossref], [Google Scholar], [Publisher]

[13] B. Bann, S.A. Miller, Chem. Rev., 1958, 58, 131-172. [crossref], [Google Scholar], [Publisher]

[14] S. Laskar, G. Brahmachari, Org. Biomol. Chem., 2014, 2, 1-50.

[15] M. Costa, T.A. Dias, A. Brito, F. Proença, Eur. J. Med. Chem., 2016, 123, 487-507. [crossref], [Google Scholar], [Publisher]

[16] H.R. Shaterian, M. Mohammadnia, J. Mol. Liq., 2013, 177, 353-360. [crossref], [Google Scholar], [Publisher]

[17] R. Pratap, V.J. Ram, Chem. Rev., 2014, 114, 10476-10526. [crossref], [Google Scholar], [Publisher]

[18] T.S. Jin, J.C. Xiao, S.J. Wang, T.S. Li, Ultrason. Sonochem., 2004, 11, 393-397. [crossref], [Google Scholar], [Publisher]

[19] S. Samantaray, D.K. Pradhan, G. Hota, B.G. Mishra, Chem. Eng. J., 2012, 193, 1-9. [crossref], [Google Scholar], [Publisher]

[20] Y. Yu, H. Guo, X. Li, J. Heterocyclic. Chem., 2011, 48, 1264-1268. [crossref], [Google Scholar], [Publisher]

[21] J. Safari, Z. Zarnegar, M. Heydarian, J. Taibah Univ. Sci., 2013, 7, 17-25. [crossref], [Google Scholar], [Publisher]

[22] A.T. Khan, M. Lal, S. Ali, M.M. Khan, Tetrahedron Lett., 2011, 52, 5327–5332. [crossref], [Google Scholar], [Publisher]

[23] A. Kumar, S. Sharma, R.A. Maurya, J. Sarkar, J. Comb. Chem., 2010, 12, 20-24. [crossref], [Google Scholar], [Publisher]

[24] J.M. Khurana, B. Nand, P. Saluja, Tetrahedron, 2010, 66, 5637-5641.

[25] F. Kamali, F. Shirini,Polycycl Aromat Compd., 2019, 41, 73-94. [crossref], [Google Scholar], [Publisher]

[26] F. Kamali, F. Shirini, J. Mol. Struct., 2021, 1227, 129654. [crossref], [Google Scholar], [Publisher]

[27] F. Shirini, N. Daneshvar, RSC Adv.,2016, 6, 110190-110205. [crossref], [Google Scholar], [Publisher]

[28] M.S. Rao, B.S. Chhikara, R. Tiwari, A.N. Shirazi, K. Parang, A. Kumara, Chemistry & Biology Interface, 2012, 2, 362-373.

[29] J. Albadi, A. Mansournezhad, M. Darvishi-Paduk, Chin. Chem. Lett., 2013, 24, 208-210. [crossref], [Google Scholar], [Publisher]

[30] M.G. Dekamin, M. Eslami, A. Maleki, Tetrahedron, 2013, 69, 1074-1085. [crossref], [Google Scholar], [Publisher]

[31] M.A. Pasha, V.P. Jayashankara, Indian J. Chem., Sect B., 2007, 46B, 1328-1331. [crossref], [Google Scholar], [Publisher]

[32] H. Kiyani, F. Ghorbani, Res. Chem. Intermed., 2015, 41, 7847-7882. [crossref], [Google Scholar], [Publisher]

[33] F. Khorami, H.R. Shaterian, Chin. J. Catal., 2014, 35, 242-246. [crossref], [Google Scholar], [Publisher]

[34] C. Yao, C. Yu, T. Li, S. Tu, Chin. J. Chem., 2009, 27, 1989-1994. [crossref], [Google Scholar], [Publisher]

[35] J.M. Khurana, D. Magoo, A. Chaudhary, Synth. Commun., 2012, 42, 3211-3219. [crossref], [Google Scholar], [Publisher]

[36] M.M. Heravi, B. Baghernejad, H.A. Oskooie, J. Chin. Chem. Soc., 2008, 55, 659-662. [crossref], [Google Scholar], [Publisher]

[37] M.M. Heravi, K. Bakhtiari, V. Zadsirjan, F.F. Bamoharram, M.O. Heravi, Bioorg. Med. Chem. Lett., 2007, 17, 4262-4265. [crossref], [Google Scholar], [Publisher]

[38] A. Shaabani, R. Ghadari, S. Ghasemi, M. Pedarpour, A.H. Rezayan, A. Sarvary, S.W. Ng, J. Comb. Chem., 2009, 11, 956-959. [crossref], [Google Scholar], [Publisher]

Eurasian Chemical Communications

Effective and convenient synthesis of 2-amino-4H-chromenes promoted by melamine as a recyclable organocatalyst

References

References

Volume 3, Issue 4
April 2021
Pages 278-290

Effective and convenient synthesis of 2-amino-4H-chromenes promoted by melamine as a recyclable organocatalyst

References

References

Volume 3, Issue 4April 2021Pages 278-290

Volume 3, Issue 4
April 2021
Pages 278-290